21 Epic Villas in Tuscany with Private Pools [Curated Picks for 2024]

tuscany villa in italy with swimming pool and luxury accommodations

With rolling hills and vineyards as your everyday backdrop, renting a Tuscany villa with a private pool is one of the best ways to experience the bucolic landscapes of Italy’s most beautiful countryside.

And with fully-equipped kitchens, al fresco dining areas, and beautiful gardens, a home’s comforts meets nature’s beauty in these villas.

Of course, the crown jewel of many of these Tuscan villas are their private pools, a little secluded sanctuary to float clear blue skies or lounge at the water’s edge with a glass of Chianti in hand.

Renting a villa in Tuscany with a private pool is not just about luxury, though it can be if you want it to be — there are plenty of luxe jewels in this list, but also some budget sleeper hits that will surprise you with how affordable they are.

a pool villa in tuscany with loungers and countryside

It’s also about embracing the experience of traveling with a group of loved ones, whether that’s the family you’re born into or the family you’ve chosen.

In between relaxing at your Tuscan pool villa, you can explore medieval towns, taste your way through the humbly decadent Tuscan cuisine, or merely indulge in the sweet art of doing nothing at all!

My Top 3 Picks For Tuscany Villas with Private Pools

#1 TOP PICK

⭐️⭐️⭐️⭐️⭐️
Villa Il Turchetto

✔️ 5,000 sq. ft. pool villa (8 bedroom 7 bathroom)
✔️ Located near Saturnia thermal springs

#2 PICK

Locanda in Tuscany

✔️ Fits up to 24 guests with 9 bedrooms & 10 bathrooms
✔️ Located in stunning Val d’Orcia with pool overlooking countryside

#3 PICK

Casa Terzerie 

✔️ Decor inspired by a Lake Como villa with Tuscan elements
✔️ 10 guest capacity with 5 bedrooms & 3,500 sq. ft.

Getting Around Tuscany

a car driving on a famous road in tuscany in autumn

These pool villas in Tuscany are pretty much impossible to reach with public transportation, and they are often in the countryside, not within walking distance of any amenities.

If you don’t want to feel isolated, you’ll definitely want to rent a car in Tuscany to make the most of your stay.

I recommend renting a car as soon as you fly into Florence (assuming you are starting your trip there), since you’ll get the best rates at the Florence airport.

I use Discover Cars to search for the best car rental prices in Italy, since they compare 500+ agencies (including smaller local ones, not just the big names) to find the best deal on your rental.

Best Villas in Tuscany with Private Pools for Large Groups

Overall Best For Big Groups: Villa Il Turchetto – Book Here

This massive Tuscany villa with private pool is the perfect choice for large groups — it can fit as many as 16 guests in its 8 bedrooms and 7 bathrooms (no bathroom hold-ups here!).

Even with a full house, you won’t be cramped at all. Villa Il Turchetto is a whopping 5,000 square feet, larger than life on the inside with high ceilings and exposed wood beams. 

The bedrooms are a variety of sizes, from smaller rooms perfect for kiddos to larger master-style suites, but truly no one will feel shafted by the rooms — they’re all very comfortable.

Some of the bathrooms even have bathtubs, for those of us who love a good soak at the end of a day on vacation.

… and speaking of good soaks, the location in Saturnia means that you’re right next to one of Tuscany’s hidden gems, the thermal springs right in town. 

When you’re this close, it’s a breeze to be there bright and early to be some of the first ones to enjoy the springs, which can get rather busy after the morning hours.

Back to this villa: with a living room with a fireplace, comfy armchairs, and a wall of built-in bookcases just begging you to curl up with a good novel, you absolutely will find yourself wishing you can move in.

The outdoor spaces here are massive too: plenty of comfortable cushioned chairs shaded by a thatched-style awning, giving you shade with hints of sun as you enjoy a Tuscan afternoon on the porch.

And of course, it wouldn’t be a trip to Tuscany without many a dinner al fresco.

Luckily, with a massive, well-equipped kitchen (I think I counted a whopping 8 burners to use on the massive, hood-range stove) and  enough outdoor seating to fit the whole crew, you’re ready to host unforgettable dinners in the cool Tuscan night breeze.

As for the pool, you won’t make any sacrifices here: it’s huge, so every single one of 16 guests could be in the pool without feeling crowded. 

It’s large enough to swim laps in, but it’s also just a wonderful place to relax in, admiring the Tuscan countryside all around you and the lovely rolling hills you can see out of every corner of your eye.

Best For Spa Lovers: Podere La Piscina – Acqua Termale e RelaxBook Here

This gorgeous villa is more like a typical Tuscan pool villa meets a full-on spa — complete with a sauna and a thermal pool and hot tub with natural spring water, it really does check all the ‘spa’ boxes!

Yes, Podere La Piscina literally has its own hot spring on the property — how’s that for a unique pool villa in Tuscany?

The spring has a constant temperature of 38°C or 100°F, so it’s perfect for visiting outside of the summer season if you want a heated pool. 

If you’re looking for a colder pool for swimming laps and cooling off on hot Tuscan days, this may not be the right villa for you in the summer months!

Some of the bathrooms also feel very spa-like, including one where two people can take baths side by side using the thermal water!

Located in the countryside of Val d’Orcia in the charming village of San Casciano dei Bagni, this is one of the most scenic areas of Tuscany to stay in.

Think of that beautiful winding road lined with trees that you likely think of the image of Tuscany, and that’s the Val d’Orcia!

The town it’s near, San Casciano dei Bagni, is part of the association of most beautiful villages in Italy.

Best of all, it’s only a kilometer away, so you can reach it on foot or with a car — so this is a great mix of a private-feeling villa yet still not feeling cut off from the delight of Tuscan small towns. 

This five-bedroom Tuscany villa with a private pool is very traditional, made of stone in the old-fashioned way (as a natural form of air conditioning) — but of course, it has regular A/C as well, because this villa will not let you miss any of your creature comforts.

Sleeping up to 10 guests, the bedrooms are great for a mix of families or a group of friends — 4 of the rooms have large double beds, but there’s one bedroom with two twin size beds.

There are many common spaces to enjoy with your group, like the large living room with three huge plush couches to gather around, all surrounding a fireplace.

This room is set in a high-ceilinged room complete with an exposed wooden ceiling with its original beams and a skylight — and a piano, in case any of you are musical!

All that plus a huge, well-equipped kitchen for making delicious meals with local ingredients and plenty of room to gather around the table, and you’ll see why this is the perfect Tuscany villa with private pool — nay, private hot springs — for larger groups!

Largest Pool Villa: Locanda in Tuscany – Book Here

This may be the largest Tuscany villa with a private pool on the list: the large house can sleep up to 24 guests in its 9 bedrooms, 10 bathrooms, and a whopping 7,500 square foot floor plan!

Included in your stay is a daily breakfast at the nearby restaurant, which you can also visit for lunch or dinner if you don’t feel up to cooking for yourself.

That said, they do have a fully-equipped massive kitchen as well as outdoor BBQ facilities, so you can opt for self-catering or going out to as many meals as you like.

The outsized villa, of course, has an outsized private pool to match: stretching nearly as long as the house itself, it’s the perfect place to swim laps or take a dip during the hot afternoons in Tuscany.

There are also lots of loungers, as well as a shaded area for enjoying the afternoons outside without worrying about getting to much sun.

The pool area also has an epic sunset view, and the rolling hills of the Val d’Orcia of Tuscany is one of the entire region’s most scenic areas.

Let’s talk about the inside, now: the villa is freshly renovated, with an updated farmhouse-inspired aesthetic in all its bedrooms. 

Some of the bedrooms even have their own fireplace or clawfoot bathtub in the room!

Best for Instagram Lovers: Marsy Lavender Farm & Villa – Book Here

What’s better than Instagram snaps of you in a lavender field? Knowing you’ll be the only one there, since it’s your own private lavender farm and Tuscan countryside villa!

Nearly every square inch of this Tuscany villa with a pool is absolutely begging to be photographed, from its huge pool with floating chairs and rolling hill views to its fringed hammocks to its lovely minimalist décor to, of course, its lavender field!

Note, of course, lavender fields are not a year-round phenomenon — expect it to be at its peak from mid-June through mid-July — so you’ll want to book those dates in particular if the lavender field is a major selling point.

Located in the countryside of Marsiliana, this 5-bedroom, 6-bathroom villa is over 2,000 square feet and has plenty of room to accommodate up to 11 guests.

Rooms all have a very boutique hotel feel, with lovely high ceilings, a muted earth tone color palette livened up by thoughtful bursts of color, and bathrooms with rain showers!

The kitchen is massive and open, perfect for entertaining a large group while you cook, as well as outdoor BBQ facilities. 

Plus, this villa has its own pizza oven — how amazing is that?

And of course, since you’re looking for a Tuscany villa with a pool, I’d be remiss to mention just how large this pool is: perfect for laps or simple afternoon swims, the entire group could be in the pool at one time and it wouldn’t feel cramped!

There are also plenty of comfortable chairs and hammocks around the poolside to curl up with a book in between swims.

Typical Villa Charm: Casa Terzerie – Book Here

This very typical Tuscany villa with private pool is simple but beautiful, and that’s just what makes it so welcoming.

The lovely Casa Terzerie has all the structure of the typical regal villas of Como, with more old-fashioned features like four-poster beds, high ceilings with exposed wooden beams, and typical Tuscan tiling.

It’s great for a medium-sized group, sleeping up to 10 guests in its 5 bedrooms, each with double beds.

It’s nearly 3,500 square feet, so there’s plenty of space to not crowd each other.

The swimming pool is huge and gorgeous, lined up perfectly with the setting sun for gorgeous sunset swims.

And while the house feels very secluded, it’s perfectly situated as there’s a delicious restaurant within walking distance, 400 meters away.

That said, you’d never have to go out for meals if you don’t want to, as there’s a huge and well-equipped kitchen as well as a gorgeous al fresco dining area perfect for big meals with friends.

Best for Dinner Parties: Villa Podere Del Grasso – Book Here

Located in Castel del Piano, this Tuscany villa with a pool is a secluded little getaway perfect for groups up to 12 — perfect for families or trips with a large group of friends.

This villa in Tuscany in absolutely massive: we’re talking six bedrooms, plus two sofa beds in the living room, so it’s easy to accommodate a large group of people. 

With an enormous private pool to swim laps in or cool off in under the hot Tuscan sun, or a fireplace to gather around inside during the cooler months, this is a wonderful all-seasons villa in Tuscany for large groups.

The villa interior is gorgeous, with high ceilings complete with exposed wooden beams, completing the rustic Tuscan vibe.

A spacious kitchen with a center island to gather around is another huge perk of this villa, as it’s easy to self-cater if you want to host dinners cooking with local, seasonal ingredients — it’d be a shame to waste Italian summer produce!

A housekeeper is available in case you need any tidying while you’re staying in the villa (note that there’s an additional  charge)

With a porch featuring hammock seats overlooking the hills, this Tuscany pool villa is the perfect place to take in the sunset and relax with a glass of local Chianti.

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Best Outdoor Sunset Space: Villa Colletto – Book Here

If your favorite time of the day is sunset, this is the perfect Tuscany villa with a pool for you: Villa Colletto has one of the nicest sunset-facing terraces I’ve ever seen!

Complete with several comfortable wicker sofas and chairs with plush pillows, arranged in a circle around a table to place drinks and antipasti on, this is the perfect place to watch the sun sink into the small, rugged mountains of the Tuscan countryside.

And after the sun sets, there’s still plenty of outdoor beauty to enjoy, like the massive dining table that’ll fit the entire group with views over the surroundings villages, only tiny pinpricks of light in the dark.

The house has 5 bedrooms and 5 bathrooms and comfortably sleeps 8 guests, though honestly, I do expect it could fit more if you asked.

The interior is absolutely gorgeous too, keeping in mind the historical feel of traditional Italian villas with some incredible design features, from ornate ceilings to chandeliers to exposed beams.

One of my favorites is a bathroom with murals painted on the wall of a Tuscan landscape, complete with an exposed wooden beam ceiling, a wrought-iron standalone bathtub, and sconce lighting.

It’s like taking a bath in another century!

The bedrooms too feel like they came out of a 19th century Lake Como villa, with exposed beam ceilings, delicate molding features, vintage furnishings, and many with en-suite bathrooms that continue the charm.

And of course, you looked up Tuscany pool villas so let’s talk about the pool: it’s simply huge, large enough to swim laps in or have a pool party in!

There’s also lots of loungers around the pool to take breaks for sunbathing or book-worming. 

And the pool also is a great sunset spot to boot — you get epic views of the setting sun and its palette of brilliant sunset colors here, too.

There are both indoor and outdoor kitchens, and you can even hire a private chef who can cook Italian classics for you.

Perhaps even better for lovers of Tuscan wine, they have their own wine cellar and can arrange for private wine tastings!

The prices for the chef and wine tasting are rather reasonable too, starting at 35-45€ per person for meals and 25-35€ per person for wine tasting.

Who knew private luxury in your own Tuscan pool villa could be that inexpensive?

Olive Farm Beauty: Chiarentana – Book Here

This charming Tuscany pool villa in Chianciano Terme is the perfect spot for large groups of up to 14 people, with 7 bedrooms and 7 bathrooms so everyone has plenty of space (2,500 square feet).

Once a fortress and a few scattered farmhouses, Chiarentana is now a gorgeous, modern place to stay with a variety of options, but we’ll focus on the villa here, since it has its own private pool.

Oh, and did I mention it’s also an olive oil farm? It doesn’t get any more Tuscan than that, does it?

The rooms are typical Italian understated villa beauty: simple but elegant furnishings that mix and match vintage with modern, so all your creature comforts are met while still having that traditional villa feel.

The kitchen is huge and spacious, high-ceilinged with lots of natural light and counter space, plus an in-kitchen dining table for entertaining and having family or group meals.

There’s also a huge living room with a fireplace and lots of seating, perfect for a night of chats, games, and drinks to match.

Best Infinity Pool: Villa Lolù – Book Now

Located in the small town of Terranuova Bracciolini, this exquisite villa in Tuscany with a private pool is perfect for a larger group of up to 9 guests.

With four bedrooms (3 queen, one with two twin) and a living room with a sofa bed, as well as two bathrooms, there’s plenty of space at this Tuscan villa so you won’t feel crowded, even if you’re at max capacity.

It’s also rather close to the Florence airport, making transfers a breeze, as it’s located about halfway between Florence and Arrezzo, another charming Tuscan city.

The interior oozes Italian countryside charm, with rustic exposed stonework in the dining room, an outdoor area perfect for al fresco dinners with endless Chianti pours, and the typical rust-red and mustard-yellow hues of the Tuscan countryside in the shared areas.

On cool nights, there’s also a fireplace to enjoy and gather around in the lovely living room — but if it’s warm, don’t worry, this Tuscan villa is complete with A/C as well!

But of course, the real draw is the private pool: beautiful day or night, this infinity pool looks over the rolling hills of Tuscany. 

And all lit up at night in beautiful turquoise and gold, there couldn’t be a better place to drink wine and chat with friends and family late into the early morning hours. 

Plus, there’s a Jacuzzi as well to use!

And if you thought it didn’t get any better, the lovely couple who runs the villa, Gaetano and Francesca, will cook for you — even making you delicious home-cooked pizzas in their pizza oven!

Private Villa Close to Town: Podere La Terminella – Book Now

Get the best of both worlds with this gorgeous Tuscany villa with a private pool just outside of Volterra, a mid-sized town in Tuscany with a lot going on.

This is the perfect villa to stay in if you don’t want to feel totally secluded out in the countryside far from all the restaurants and attractions of Tuscany, but you still want the privacy and spaciousness that a pool villa gives you.

With 6 bedrooms and 8 bathrooms, this Tuscany pool villa comfortably fits up to 12 guests, making it great for groups of friends and families.

One of its best features is its infinity pool, which looks straight over the rolling landscape of the Tuscan countryside for some of the best views you can imagine.

Next to the pool, there are loungers with large umbrellas perfect for sunbathing with views of Tuscany spread out before you.

There’s also a large outdoor al fresco dining area, so you can eat lunch and dinner with the same sweeping views!

Inside, the kitchen is a modern marvel — you’ll find yourself wanting to cook in this one, with its gorgeous marble countertops and endless counter space, fully equipped to make mouthwatering meals.

There’s a wonderful little breakfast nook, multiple fireplaces, and tons of spacious seating areas to enjoy indoors.

The bedrooms are also very spacious and modern, with high ceilings with wooden beams and en-suite bathrooms with soaking tubs or walk-in showers — the ultimate in relaxation!

Best for Families with Little Kids: Villa Antico Borghetto Di Tigliano – Book Here

This old-fashioned Tuscany villa with a private pool is an affordable choice for mid-sized groups, fitting up to 8 guests in this 4-bedroom, 3-story villa.

A 10-minute drive from the charming Tuscan town of Vinci, it’s conveniently located but still feels very private and secluded. 

You can enjoy the large, spacious garden and its BBQ facilities as well as its above-ground pool, accessed via stairs that can be gated off.

This makes it an especially safe choice for families with young kids who may be worried about the safety of a Tuscany pool villa.

For an above ground pool, it’s rather large, and while you wouldn’t necessarily be able to swim laps in it, it’s definitely not a kiddie pool!

Kids will also love the treehouse-style play structure complete with a slide!

In terms of the interior, think old-fashioned Italian comforts: iron-wrought furniture, oil paintings and prints of famous Italian artists, and the typical Tuscan color palette of pale yellow, brick, and rust-red.

It’s not the most design-forward Tuscany pool villa, and fans of modernist design will definitely find it a little dated, but if you want old-fashioned charm, this is it!

Modern Beauty with Spa Features: Villa Le Terme – Book Here

This pool villa in Tuscany doesn’t quite feel like the others, as it has a really modern architecture compared to the others, which are more traditional in their design.

While it may not ooze with historic charm the way many of these Tuscany villas with private pools do, Villa Le Terme still is an excellent choice and may be better for those with more modernist design sensibilities.

It’s also great for large groups, with 5 bedrooms, 6 bathrooms, and the ability to fit up to 13 people. One bedroom is on the ground floor and is wheelchair accessible.

This villa boasts not one but two pools: one outdoors with a gorgeous view, and one indoors, covered with a roof but surrounded by glass windows so you won’t feel like you’re missing a bit of the view!

Plus, there’s also an indoor dry sauna as well as a Turkish bath steam room to complete the “home spa” feel, as well as two tiled hammam-style relaxation loungers in the indoor pool area.

The outdoor pergola is very modern, with geometric, clean-lined outdoor furniture for lounging and relaxing beside the huge swimming pool.

Inside, the kitchen is compact but very functional, with plenty of counter space and all sorts of modern appliances that wouldn’t look out of place in a brand-new luxury apartment.

That same modern aesthetic continues throughout — from the loft-style feel of the living room-meets-dining area to spacious, minimalist bedrooms, this definitely feels like a 21st-century villa.

If you’re looking for the romantic, historic villa in Tuscany — this isn’t it. But if you want a large space and a private pool with a modern feel, this is a great choice!

Typical Tuscan Vibes: Villa Mezzavia – Book Here

Located outside the popular Tuscan destination of Cortona, this Tuscany pool villa is huge — over 3,000 square feet — with 6 bedrooms that can welcome up to 11 guests.

The two-story Villa Mezzavia has a massive private pool on site, with lots of sun loungers aside it for sunbathing in between swims.

The huge pool is well-shaded by trees for much of the day, so it’s perfect for swimming on hot days without worrying about the scorching sun!

The interior is spacious and traditional, with your typical Tuscan tile floor and brick-lined archways that given an open floor plan feel while still having separate ‘rooms’ in the main living area.

The kitchen is well-appointed though a little small, but you can definitely make do for cooking some nice meals in here to be enjoyed either in the dining room in the main house or al fresco.

The bedrooms continue the traditional Tuscan aesthetic, incorporating the same tile and brickwork in the rooms, whose edges are softened with vintage furnishings that make you feel like you’re staying in another century.

And some bedrooms even have a soaking tub in the room, whereas others have an en-suite bathroom with a step-in shower.

Small Town Bliss: Villa La Casa del Re – Book Here

Just outside the small town of Le Piazze, you can easily run into town for the things you need — a coffee, a bottle of wine, some food, all 10 minutes away on foot.

Yet still, Villa La Casa de Re is set away back far enough that you can feel the seclusion of having your very own Tuscany villa with a private pool.

Taking up 3 floors, this 6-bedroom villa can sleep up to 11 guests comfortably, though smaller groups can enjoy it as well. 

Though given how many people it can fit, it can be a rather cheap price per person if you have a full house!

The interior is lovely, warm, and welcoming, with bright white walls that invite in the natural light and wooden exposed beams that give the whole room a lovely rustic feel.

The kitchen is spacious, perfect for making a meal with a group of friends, as well as having an outdoor BBQ area for delicious summertime meals.

The pool is not huge, but it’s large enough to enjoy with a smaller group, and there are plenty of sun beds and umbrellas for you to enjoy some sunbathing.

The bedrooms have the same high-ceilinged, minimalistic yet warm stylings as the rest of the house, simply furnished with beautiful wooden furnishings and uncluttered so they have a peaceful feel.

That said, the bathrooms feel a little dated, as the tile is bit old-school and the showers aren’t particularly nice or modern.

Best Villas in Tuscany with Private Pools for Smaller Groups

Best for Budget Travel: Le Rime di Campagna – Book Now

Just on the outskirts of the charming Tuscan city of Arrezzo, less than 3 miles from the city center, you’ll find this lovely Tuscan villa for quite an affordable price!

This budget-friendly villa in Tuscany with a private pool has everything you’d want — air conditioning, a well-stocked kitchen and BBQ facilities, a patio with views of the rolling hills, and an outdoor fireplace — all at a reasonable price that’s perfect for a smaller group.

With two bedrooms, two bathrooms, and the ability to fit up to four guests, this is a great choice for two couples traveling together or a family of 4 who wants a bit of privacy during their stay.

The design is subtle and homey, not over-the-top fancy, but that’s part of its charm — it makes your Tuscany pool villa feel a little more like a home away from home, at least for a time.

The pool is not incredibly large, but since it’s a private pool for just your group of four or fewer to use, that’s not such a bad thing…

Especially when there’s an outdoor dining area and a hammock area to enjoy just next to the pool!

If you want the Tuscany villa with a private pool experience without the huge price tag, this is the spot for you, so long as your group size is small enough to make it work!

Stone House Budget Beauty: Villa La Pergola – Book Here

In a typical stone home you’ll find all over the Tuscan countryside, surrounded by flowering trees and vines, the beautiful Villa La Pergola is a good option for smaller groups of 6 or less.

With 3 bedrooms — two double beds and one sofa bed — and 2 bathrooms, this is a spacious villa in Tuscany with a private pool despite the lower number of bedrooms compared to most, with a nearly 3,000 square foot floor plan.

The interior is quintessentially Tuscan: exposed stone walls that show off the masonry, juxtaposed against plenty of wood details and mustard yellow and rust red accents.

The bedrooms are that perfect blend of minimalistic yet not Spartan, with plenty of room to spread out in yet with enough personality and detail to feel individualized and homey, like you’re staying in the house of a family friend.

Admittedly, the circular swimming pool isn’t the largest, but it’s perfectly suitable for a dip to cool off on a hot Italian afternoon.

There’s also a great pergola — who would have guessed it from the name of the villa? — with a large dining table for meals under the Tuscan sun (or stars).

But best of all is the price, which can be downright affordable; sometimes the villa is available for under $250 per night, which is just over $40 per person per night if you have a full house!

Hillside Beauty: Villa Ada Belriguardo – Book Here

Located in the countryside, this charming Tuscany villa with a private pool is set on the hillside amidst beautiful gardens, close to the towns of Sarteano and Cetona.

Typical of villas in the region, Villa Ada Belriguardo is made of stone with a terra cotta roof, emblematic of the Tuscany region.

The pool is located a terrace or two below the villa and it is simply massive, overlooking a valley of Tuscany’s hilly region. 

There is plenty of room for the whole group to enjoy the pool, or to swim some laps if you’re looking for exercise.

The pool is also beautifully lit up at night, perfect for night swims under the uncountable stars of the Tuscan sky.

This villa is on the smaller side in terms of how many guests it can fit: with only 3 bedrooms and 2 bathrooms, it’s better suited for smaller groups of 6 or fewer.

That also makes it a fairly affordable place to stay on a budget, especially if you have a full house, though it isn’t the cheapest villa on the list.

The interior of the villa is beautiful in an old-fashioned way: think Tuscan tile floors, iron-wrought bed frames, and vintage wooden furnishings.

The bathrooms are a little small and dated, but the rest of the house feels spacious, recently renovated, and inviting, especially the kitchen and living areas.

Plus, there’s also a game room complete with a pool table!

In short, as long as you don’t need the most modern of design choices, this is the perfect choice for a smaller group looking for a Tuscany villa with a private pool.

Close to Florence: CountryHouse con Piscina – Book Here

Just on the outskirts of Florence near the outer suburb of Rifredi, you can have your own Tuscan villa with private pool while just being a short ride into town — less than 4 kilometers to its main sights, in fact.

In fact, it’s so close to the center of Florence that you can just walk to the tram, which is 5 minutes walk away, and that’ll sweep you right into town!

With a private indoor pool surrounded by beautiful brick and stone, complete with hydromassage jets, this is a lovely place to relax after a busy day sightseeing in Florence — and it’s lit up beautifully at night, giving it an almost hammam-style feel.

The indoor pool is a bit small, but it’s definitely suitable for relaxing in after a full day of sightseeing around the city.

Plus, the villa also has an outdoor fireplace, a BBQ area, and some garden areas to walk around, so you really will feel like you’re outside of the urban center, despite being so close to it!

Of course, being so close to Florence, you do make a sacrifice: namely, space, as the country house is a little on the small side. 

The rooms can be a little narrow, as everything fits in a 600 square foot floor plan, but nevertheless this charming tiny house fits up to five guests comfortably in its 2 bedrooms (and a living room sofa bed).

But for the price and location, it’s a great offer — just don’t expect a massive villa or an outdoor pool, because that’s not what this villa is about!

Renting a Car in Tuscany: 15 Essential Tips & Tricks From an Italy Local

View of a road in Tuscany overlooking a vineyard

Tuscany is truly an essential vacation destination for every visitor to Italy!

Hilltop villages with medieval architecture, rolling foothills extending as far as the eye can see, and long country roads lined with cypresses: it all adds up to make Tuscany an incredible destination that can’t be missed.

Tuscany’s capital city of Florence may be one of the most visited cities in the Mediterranean country, but the region has so much more to offer (Tuscan wine tour, anyone?).

Tuscany’s charm lies not only in its big-hitters like Florence and Siena, but also in its smaller villages and towns, which are best seen by renting a car in Tuscany and exploring it by road trip. 

Landscape of the Tuscany seen from the walls of Montepulciano, one of the most scenic towns in Tuscany
With charming towns like Montepulciano, renting a car in Tuscany is a no brainer

Of course, Hollywood movies have done a fantastic job romanticizing the region, and rightly so.

With that said, whatever you expect from this Italian region, it’s sure to live up to (and exceed) even your wildest dreams. 

So, now that you’re (hopefully!) convinced that you need to get to Tuscany ASAP, let’s start planning the perfect way to explore it: a road trip through Tuscany, of course!

During the fifteen years I spent living in Italy, I traveled to Tuscany several times, mostly via car, and I know I’ve still got more to discover about this gorgeous region. 

In this guide, I am so excited to share everything you need to know about renting a car in Tuscany, including some Tuscany-specific driving tips.

About Italy’s Tuscany Region

Duomo in Florence, with rounded building and marble artwork with stripes and symmetry
Florence may be Tuscany’s capital, but it’s only the beginning what this region has to offer!

So, let’s start with the basics! Tuscany is a gorgeous region in central Italy, best known for beautiful cities, delicious cuisine, charming medieval villages and rolling sun-drenched hills covered in vineyards. 

The capital of Tuscany is Florence, a city often referred to as the birthplace of the Renaissance. 

And that’s no surprise — home to countless famous landmarks and works of art, including the original of Michelangelo’s Statue of David.

David is a Renaissance sculpture masterpiece of Michelangelo in florence italy, shown in the Accademia Gallery
The Statue of David — one of Florence’s most famous and long-enduring residents!

With its stunning architecture and superb museums, the Tuscan capital is one of the best cities to visit if you’re looking to really dive into Italian history.

You simply must spend at least one day in Florence before leaving for your Tuscany itinerary!

Aside from Florence, Tuscany is home to many popular tourist spots such as Siena, Pisa, San Gimignano, and the Chianti Region, which all make great day trips from Florence or stops on a Tuscany itinerary.

Across Tuscany, you can visit eight World Heritage Sites and countless nature reserves to admire the gorgeous countryside.

The sheer variety of historical, natural, and cultural sites in Tuscany makes it one of the top regions to visit in Italy — and the wealth of great accommodations, like these villas with private pools, make it an even more epic place to stay.

While you could easily spend several days or weeks discovering Tuscany’s most important cities, your trip wouldn’t be complete without exploring the picturesque countryside on winding backroads.

Do You Need to Rent a Car in Tuscany?

Typical Tuscany landscape with grain fields, cypress trees and houses on the hills at sunset. Summer rural landscape with curved road in Tuscany, Italy, Europe
You’ll need to rent a car in Tuscany for views like this one!

If you want freedom of movement and the chance to explore more than just the major cities, renting a car in Tuscany is the way to go. 

You could also get around by train or bus, but you’d miss out on all the stunning landscapes and delightful little villages.

Of course, whether or not it’s worth renting a car in Tuscany also depends on how much time you have.

If you just want to visit Florence (Firenze) and maybe a couple other nearby towns, you can do that just by taking a Tuscany tour as a day trip.

Driving in big cities in Italy can be a waste of time and energy, so it’s better to get around by public transport.

However, once you start to tally up your wishlist of the smaller towns that make Tuscany so charming, public transport can be more trouble than it’s worth.

If you’re short on time or have a lot of smaller towns and wineries planned for your trip, renting a car is the best option to make the most of just a few days in Tuscany.

View of a road in Tuscany overlooking a vineyard
Renting a car lets you pause and enjoy Tuscany’s small towns and wineries!

Checking out your options for renting a car in Tuscany only takes a few minutes, but this guide will help you make the right choice and avoid any logistical headaches or last-minute complications!

First of all, who to rent with? I always pick Discover Cars to search for the best deal for car rentals in Italy for multiple reasons.

In short, it has the widest selection, the clearest prices, the best cancellation policy, and the most affordable full coverage insurance.

🚗 Best Tuscany Rental Car Prices: Discover Cars

This search engine not only looks at the typical rental car agencies (which can be $$$), it also looks at local, small Italian agencies that may offer better deals. Their pricing is straightforward (no bait-and-switches) and they offer free cancellation if you need it.

➜ Check rental prices in Tuscany with Discover Cars here!

Things to Know About Driving in Tuscany

Although the rental process is basically the same as other countries, there’s a few country-specific aspects to be aware of, as well as some things about driving in Tuscany in particular. 

Here are the most important things to know before renting a car in Tuscany!

Roads in Tuscany

highway sign with the signs of the junction to go to Florence on the panoramic road or on the Direttissima road (a direct route that is not as scenic)

In Tuscany, you’ll likely drive on all kinds of roads, from motorways (autostrade) to narrow roads passing through small villages. 

The motorways have tolls, but they’re your best option to get from one place to the other quickly.

There are three motorways that run across Tuscany. The A1 motorway is Italy’s longest motorway, as well as the oldest in Europe! 

This motorway connects Milan to Naples and passes by Florence.

The other two motorways are the A11 from Florence to Pisa (Firenze Mare) and the A12 from Cecina to Genova.

A vintage Italian Fiat 500 convertible car drives along a typical Tuscan tree-lined avenue
The scenic backroads of Tuscany are the best part!

While the motorway may be the fastest option, the smaller regional roads are far and away the most scenic.

In particular, the Via Chiantigiana is the region’s most beautiful road, connecting Florence to Siena. 

The road passes through the beautiful Tuscan wine region of Chianti Hills (Colline del Chianti). 

If you decide to rent a car, driving along this road is a must, and make sure to leave yourself plenty of time to enjoy the scenery!

Best Place to Rent a Car in Tuscany

A road in tuscany going through the landscape
Driving in Tuscany means taking scenic backroads like this!

You can rent a car in most cities in Tuscany, such as Florence, Siena, Arezzo, Pisa, and Lucca

Even easier, the international airports of Florence and Pisa also have several car rental companies, so you can pick up your car as soon as you land!

You’ll also generally find the best prices at these international airports, since there is more competition than in cities that don’t have airports.

Depending on the season, you really need to book a few weeks in advance, especially if you want to pick up your car in one of the smaller cities or if you must have an automatic transmission car (more on this later). 

Florence and Pisa have more options, so you may be able to find a car here even on short notice, but I’d still book early just to be careful — luckily, Discover Cars has free cancellation so you’re not on the hook if your plans change.

Cost of Renting a Car in Tuscany

Winding country road in rural landscape with cars, view of town in the distance beyond the road
Book your rental car early to get the best prices, especially in high season

The cost of renting a car in Tuscany can vary greatly depending on the season and how far in advance you book. 

You can expect to pay between $35 and $90 per day for economy cars, and well over $100 daily for bigger ones.

Usually, airport rentals are cheaper (check prices at Florence Airport or Pisa Airport here), even if you only book a few days in advance. 

Rentals in the city center of Florence or Pisa can cost a lot more, even twice the rates of airport rentals, so you should definitely check all the options if you’re looking to save money.

One more note on cost: on top of the base cost for the rental, you’ll have to factor in the cost of full insurance coverage (typically around $7/day if bought with your rental) and the gas you’ll use. 

Unfortunately, in recent years, the price of fuel in Italy has increased significantly like in much of the world, so be prepared to pay at the pump!

Car Rental Insurance

Bolgheri famous cypresses trees straight boulevard landscape
Full coverage is inexpensive and gives you peace of mind on the road!

Collision Damage Waiver (CDW) is included by default in every car rental because it’s mandatory in Italy. 

However, this only covers the car’s bodywork in the event of an accident, and even then, it usually has a pretty high deductible that you’d have to pay out of pocket.

For just a few extra dollars — typically about $7 a day with Discover Cars — you can get full coverage.

This covers, well, everything fully: not only accidents, but theft, damages ranging from a small chip in the windscreen to major repairs, and even inconveniences such as replacing lost keys. 

Full coverage is not mandatory but can come in handy, especially for those minor incidents that are more likely to happen.

Why not protect your road trip from any bad luck with a little planning ahead?

Necessary Documents for Car Rental

An international driving permit and car keys
Coming from the US or Canada? You’ll need an IDP!

The documents required to drive in Tuscany vary depending on your nationality. 

European travelers can drive in Italy with their driving license, while most travelers from outside the EU, including US and Canadian citizens, will need an international driving permit (IDP).

You have to obtain the IDP before traveling to Italy, so be sure to take care of that when booking your trip.

Americans can obtain their IDP through AAA’s website; other nationalities can check here.

To rent a car in Tuscany, you’ll also need your passport (or ID for EU citizens) and a credit card. 

Some rental companies accept debit cards now, but they’ll require a really hefty deposit that you won’t get back until several days after the end of the rental period.

It’s far better to use a credit card to avoid this big deposit, since they will just place a hold for the deposit as opposed to actually taking out the deposit.

The Best Car Type for Driving in Tuscany

Person's hand on an automatic transmission car
If you can only drive automatic, be sure you don’t accidentally book a manual car!

When choosing your rental car for Tuscany, you should consider two things: transmission type and car size. 

Unlike the US, most cars have a manual transmission in Italy, so pay attention to this detail when booking your car. 

Typically, automatic transmission cars are a bit more expensive than manual cars since there are fewer of them in Europe, where most people drive manual cars.

However, if you’re not used to driving cars with manual transmission, or if you just don’t want to worry about it, it’s worth paying a little extra for a smoother driving experience.

Last but not least, a good guideline when renting a car in Italy is that smaller is better.

Old vintage car on a street of Tuscany, a small car suitable for small roads
Go as small as you can when renting a car in Tuscany

Of course, the ideal car size for your rental will depend on how large your group is and how much luggage you have.

No matter how cute it is, that family of 4 with young kids won’t fit into a Fiat! It’s just not happening.

Luckily, there’s a wide range of options available, from zippy little Fiat 500s (an Italian classic – especially the convertible kind!) to mid-range sedans to SUVs.

In general, renting a smaller car will make it easier to drive along the narrow streets of the Tuscan villages, especially when it comes time to find parking!

Navigating the Roads in Tuscany

Famous winding road with a car driving in Tuscany, Italy in summer with dry fields that have recently been razed
Navigating in Tuscany isn’t too complex, but you’ll still want offline maps downloaded!

Driving on the motorway or big roads outside urban areas is fairly easy. You’ll find signs to guide you along the route no matter where you need to go.

Additionally, navigation apps like Google Maps will help you get around without problems.

However, always (and I do mean always) check traffic signs, especially when driving in the city.

Be aware that on Italian motorways, road signs point to highways that go to specific cities, not cardinal directions like we may be used to in the USA. 

Unless you plan to use a navigation app, take a moment before you start driving to double check the map and see in which direction you need to drive.

For instance, to drive from Florence to Arezzo, you must take the motorway toward Rome.

You should be sure to download an offline map in case you get lost and have no service on your phone to check Google Maps.

Driving through areas in the countryside where you get little or no coverage is not uncommon, so I definitely recommend this backup plan!

The Best Time for a Road Trip in Tuscany

Fall in Tuscany with vineyards turning beautiful orange and yellow colors
Fall in Tuscany is the perfect time for a road trip!

Although you can go on a road trip in Tuscany any time of the year, spring and fall are the best seasons. 

Summer is a great time, especially with the gorgeous Mediterranean weather, but you’ll face big crowds in all the most popular attractions and much higher prices across the board to match the increased demand.

The downside of a road trip in winter is that it can be rainy and quite cold.

Snow is uncommon in Tuscan cities and even in the countryside, but occasionally at higher altitudes, you may find a bit of snow, which can make driving slightly more complicated.

In spring, the weather is pleasant, especially if you visit from Mid-April to late May. 

If you decide to visit Tuscany in the fall, October is the best month.

Especially towards the end of the month, the Tuscan countryside’s rolling hills take on vibrant fall colors that make them even prettier.  

Where to Go on a Road Trip in Tuscany

the beautiful town of volterra in italy
Towns like Volterra are a must-visit in Tuscany!

In addition to visiting Florence and the other big cities in Tuscany, renting a car will give you the freedom to discover delightful little towns such as Montepulciano, Pitigliano, Volterra, and San Gimignano.

The most picturesque drive in the region has to be along the Via Chiantigiana, which passes through the Chianti Hills and small villages such as Greve in Chianti, Castellina in Chianti, Montefioralle, and Radda in Chianti.

Last, but certainly not least, you can explore the Tuscan seaside with its lovely coastal towns, like Forte dei Marmi, Viareggio, and Orbetello.

Whether you only have a few days or a couple of weeks, renting a car in Tuscany is surely the best way to experience this stunning region.

If you want a jumping off point to plan the perfect Tuscan itinerary, we have a five-day Tuscany road trip itinerary here, with ideas on how you can extend your stay beyond that.

Important Driving Rules in Tuscany

View from car to the Tuscany wine fields, you can see the rearview mirror and someone taking a photo in the mirror.
Read up on how to avoid fines and you’ll have a stress-free time in Tuscany!

Driving in Tuscany is generally a pleasant experience — as long as you’re aware of important rules you’ll want to follow to avoid fines.

These can be hefty — trust me, as someone who has paid several Italian traffic tickets — and they hit even harder when your rental car agency adds on their own fees for handling the ticket on your behalf.

Aside from that, driving in Tuscany is pretty breezy. The streets are in good condition, and the weather rarely gets too extreme. ‘

The only places that can be slightly stressful to drive are the cities and small villages with narrow streets, but here’s where that smaller rental will really come in handy!

Lucky for you, I’m here to take you through the most important driving rules so you can make it through your Tuscany road trip without inconvenience.

Limited Traffic Areas

Restricted traffic zone road sign in Italy for the historic center
Avoid ZTLs and you’ll be safe!

The biggest thing that most foreigners will struggle with when driving in Tuscany is the ZTL.

The acronym stands for Zona a Traffico Limitato, which translates to “limited traffic zone”.

These areas are clearly marked with signs and monitors indicating whether the limitation is active.

You’ll usually find ZTL in the historic centers of big cities, such as Florence. If you notice a sign stating “ZTL Attiva,” steer clear of  driving there!

These areas are equipped with cameras, so you’ll get a fine if you don’t respect this rule.

The ZTL is usually only active during certain times of the day, or on specific days of the week.

If you see “ZTL Non Attiva,” you’re all clear to drive through. You’ll also find signs stating on which days and time intervals the limitation applies.

Keep in mind that your phone will likely ignore the ZTL and keep trying to direct you to drive on limited roads — ignore this, go around, and let your phone re-route you.

Parking

Old-fashioned green car in courtyard of brick house in a typical Italian countryside style village
Not only are smaller cars cute, they’re convenient for parking!

Parking in big cities, especially in or around the city center, can be really tricky.

The first thing to keep in mind is that parking lots have different colored lines marking spaces — and these colored lines likely differ from what you’re used to back home. 

Parking lots with white lines are free, while blue ones have a fee. Yellow lines signal parking spots dedicated to disabled people or for unloading.

For paid parking, you’ll find ticket machines within a short distance. Always carry coins, as most of them don’t take a card and don’t give change! 

Parking spots usually have specific periods of time when they require payment. You’ll notice that most of them are free after a certain hour in the evening. 

Keep an eye out for signs to see when you can make the most of this free parking!

If you’re looking to keep things simple and smooth, the easiest way to book a parking lot and pay online is by using the app EasyPark.

Road Tolls

Lanes on the motorway with yellow lanes demarcated for the Telepass users
You will likely end up taking some toll roads in Italy — here’s what to know

If you plan to drive exclusively on small country roads, you probably won’t have to worry about toll booths.

However, if you’re going to drive on the motorway, it’s important to know that you’ll have to pay tolls.

Don’t worry, though! The process is super simple. You just take a ticket at the booth when entering the motorway, and pay the corresponding amount when you exit.

You’ll also notice yellow signs dedicated to Telepass users.

These are only for cars with a transponder connected to the Telepass system, so unless your rental includes one, follow signs for booths dedicated to cash and card payments.

Lastly, don’t forget to carry cash for the tolls!

Most toll booths accept card payments, but it’s not unusual for them to be out of service or not accept certain cards, so it’s always better to have some cash.

Autovelox vs. Tutor

A sign showing that the speed limit is 50 km per hour with a blurry city in the background
Keep an eye on your speed when driving in Tuscany!

Always (and again, I do mean always!) respect speed limits when driving in Tuscany.

These can vary greatly, but usually, the limit is 50 km/h in urban areas, 90 km/hr on major roads outside the urban area, and 130 km/hr on the motorway. 

Certain navigation apps will notify you if you drive faster than the allowed speed limit, but always check the road signs to be sure.

Remember for Italy (and everywhere, really): what you see on the road always trumps what you see on an app!

Surpassing speed limits can lead to big fines, so don’t risk it. Speed cameras (“autovelox” in Italian) are common on most roads. 

In addition to these, motorways are also equipped with safety tutors, which also keep tabs on your speed.

The tutor system takes pictures of the license plate at two points along the highway and calculates the average speed on that portion.

If your average speed is higher than the limit, you’ll get a fine. 

This means you should always drive within speed limits, even in the absence of speed cameras or police.

Drinking and Driving in Tuscany

Two glasses of wine overlooking fields and vineyards in Tuscany
Wine tasting in Tuscany is a must — but be sure you drive safely!

Of course, a road trip in the Tuscan countryside is practically synonymous with wine tasting.

How could you pass up a chance to try some of the world’s best wines, right where they’re made?

Before enjoying a glass (or two) you must be aware of the laws on drinking and driving in Italy, not just to avoid fines, but also for your own safety.

An ABV over 0.5% will get you a fine in Italy, so always stay below this limit. At the most, you can have a glass of wine with your meal if you need to keep driving. 

With that said, the best way to avoid issues and make the most of your trip  is to schedule your wine tastings at the end of the day after you’re done driving.

You can find many places across the Tuscan countryside to enjoy wine tasting and spend the night. 

The Chianti Hills are dotted with gorgeous villas, castles, and family-owned structures (agriturismi), where you can stay overnight, tour the vineyards, and sample delicious wine. What more could you ask for?

3 Day Florence Itinerary: How to Visit Florence & Tuscany in 3 Days

florence duomo with bell tower and face of the Florence duomo

Remarkable capital of the arts, Florence is among the most important cultural centers in Italy.

It’s also the capital of the Italian region of Tuscany, one of the most important centers in the country when it comes to phenomenal gastronomy and stunning wines!

 Planning your trip to Florence at the last minute?

Here are my quick picks on what to do & where to stay!

🍷 Top Florence Experiences:
1. Tuscany Wine & Food Tour with Guide (#1 day trip!)
2. Florence Duomo Visit & Bruneschelli Dome Climb (#1 attraction!)
3. Art Tour of the Uffizi & Accademia (see the Uffizi & Statue of David)

🏨 Best Florence Hotels:
1. Cicerone (charming central Florence guesthouse)
2. Piccolo Borgo Antico (quiet studios near Boboli Gardens)
3. Hotel Unicorno (beautifully revamped 17th century building)

✈️ Flying in? Book an airport transfer with Welcome Pickups — they’ll greet you at the airport, help with bags, & bring you into the city, all pre-booked!

Florence can be a great day trip from nearby cities, such as Rome and Milan, but it is even better as destination on its own with plenty of places to visit.

When planning your Italy itinerary, you really ought to devote at least two days to Florence and its many landmarks and attractions and one extra day to the gorgeous, verdant landscapes of Tuscany and some of its medieval towns!

A road in tuscany going through the landscape

With this Florence itinerary, you will be able to combine seeing some of the richest artistic heritage in the country with tasting the incredible wine and culinary scene Tuscany has to offer.

In this Florence travel guide, I’ve written out all the unmissable things you can do in Florence and Tuscany in 3 days… let’s go!

What to Know Before You Visit Florence

view of the duomo of florence as well as the rest of the historic town from a viewpoint on the other side of the river

Florence, known as Firenze in Italian, is one of the most spectacular cities in all of Italy, especially when it comes to culture!

Florence has been home to several of the most important figures of Italian art and culture, including Dante, Donatello, Michelangelo, and many other famous Renaissance-era artists.

This gorgeous Renaissance Italian city is situated in the central part of Italy, about two hours from Rome by train, and at about the same distance from Venice and Milan, making it easy to reach from virtually anywhere in the country. 

Florence is compact, small, and quite pedestrian-friendly for those who enjoy discovering new places on foot.

However, that doesn’t mean you will be short of things to do. On the contrary! There never seems to be enough time to get bored in Florence.

The city is populated with stunning buildings, some of them really impressive, such as the Santa Maria del Fiore Duomo, or the many medieval stone bridges that cross the Arno River

Florence proudly houses some of the most perfect examples of Renaissance art in Europe, including Michelangelo’s David, the numerous paintings inside the Uffizi Gallery, as well as many picturesque churches, gardens, and piazzi

sampling different florence tuscan wines

The city is also the capital of the Tuscany region, a worldwide known wine-making area in the country (and you should definitely do a Tuscany wine tour from Florence during your visit!)

Tuscany also hosts other famous and beautiful small towns within a short train ride from Florence, which you can easily visit in a day, as well as larger cities nearby such as Pisa, Bologna, and Siena.

If you have more time in the region, follow this 5 to 6 day Tuscany road trip itinerary.

You could even stay at one of these gorgeous villas in Tuscany with a private pool!

Getting to Florence, Italy

the train station in florence with signs that say firenze s.m.n.

It is quite easy to reach Florence by train from any other city in the country. Rome is a 2-hour train ride away, while the train journey from either Milan or Venice lasts about two hours and a half.

Florence International Airport is well-connected to several European capitals through many low-cost companies.

However, if coming from overseas, note that Florence does not receive flights from non-European countries.

In that case, flying to Rome or Milan and then connecting to Florence by train or by bus are the best solutions.

Best Time to Visit Florence

a small cappuccino enjoyed outdoors on a rooftop terrace with a view of the duomo in the distance

Florence welcomes tens of thousands, if not more, visitors every month of the year!

As is usual in most Mediterranean countries, visiting is most pleasant in spring, when you won’t have to battle high temperatures and attractions are not overcrowded. 

Late April and May offer plenty of sunny days, almost no rain, and mild temperatures.

If you have to come in summer, June is best, followed by July. I suggest avoiding August, as summers are very hot in Italy.

Also, most Europeans choose to tour Italy during their August summer vacation…. and many Italians choose to go on vacation in August as well, leading to lots of shut restaurants and more!

Autumn is also a good alternative, especially from mid-September and all throughout October.

Winters can be quite cold and drizzly, but there is rarely snow in this area of Italy, so it can be a good time to take advantage of reduced fees for accommodation and many attractions, especially if you don’t mind some cold weather!

Where to Stay in Florence: Best Areas and Suggested Hotels

a street in downtown florence with the sign piazza del pesce and historic buildings

It won’t be difficult to find a good accommodation to stay in Florence, as there are many hotels, guest houses, and rental homes available in town!

However, booking in advance is always a wise thing to do. Florence is one of the most visited cities in the country all year round, so booking well in advance will guarantee you the possibility to choose better rooms at more affordable rates.

For a city with such a large international reputation, Florence is small and easy to navigate — you’ll get the lay of the land of Florence in 2 days quite easily.

It’s divided in two by the River Arno which creates two main areas where to stay: the old historic district and Oltrarno (which, in Italian, means “on the other side of the Arno River”). 

The first area, the historic part of town, is often more crowded and touristic since it hosts some of the most visited landmarks in Florence.

Despite being a busy spot in town, it is in a great central location allowing you to comfortably access every corner of the city. The area also has many hotels for every budget. 

For instance, Cicerone is a comfortable guest house with great reviews, in the heart of the city center, perfect for solo travelers and small groups!

Check rates and availability here!

The Oltrarno district, instead, is quieter and has a more local vibe. It hosts a few hotels but also several rental homes and vacation apartments, perfect for a longer stay or simply a more relaxed kind of stay. 

Piccolo Borgo Antico is a small but cozy apartment in the Santo Spirito district of Oltrarno offering easy access on foot to the gorgeous Boboli Gardens.

Check rates and availability here! 

The area near the train station, known as Santa Maria Novella can also be a good place to stay. It is not as crowded as the train station in Rome or Milan, and certainly, it is not as a dangerous place. 

Budget travelers can find plenty of accommodation choices in the area, for example, Hotel Unicorno, a 3-star hotel set in a building dating back to the seventeenth century, is only steps from many of Florence’s celebrated attractions.

Check rates and availability here!

Day Trips Worth Taking from Florence

the cinque terre area of italy not too far from milan - a good addition to a milan itinerary. colorful houses perched on a seaside cliff with flowers and harbor.

Being in such a central position in the Italian peninsula, Florence offers plenty of opportunities for day trips not just to the Tuscany region but also to other neighboring areas of the country, making it easy to escape to Rome, the Cinque Terre, or even Venice for the day.

Popular places to visit around Florence include Pisa, with its magnificent leaning tower and basilica, as well as the medieval cities of Siena and San Gimignano.

Additionally, in nearby Liguria, Genoa and the glorious Cinque Terre can also be reached by train in a little more than an hour.

In this 3-day Florence itinerary, I’ve included a day trip on the last day to the winemaking region of Tuscany with stops in some of the above-mentioned medieval towns.

There are plenty of organized trips to discover the Tuscan wine country, visit farms and wineries, and taste some authentic food from the region — this is the best way to do it, unless you prefer to rent a car and explore Italy independently.

Driving in Italy can be… well, chaotic, especially with via controllati (I once had to pay 150 euros in fines and another 150 euro in “administrative fees” for driving on the wrong road in Bologna).

If you’re just needing a car for one day, I’d suggest taking a guided tour. If you plan to drive around more of the region on a longer trip, I recommend renting a car in Tuscany.

🚗 Best Tuscany Rental Car Prices: Discover Cars

This search engine not only looks at the typical rental car agencies (which can be $$$), it also looks at local, small Italian agencies that may offer better deals. Their pricing is straightforward (no bait-and-switches) and they offer free cancellation if you need it.

➜ Check rental prices in Tuscany with Discover Cars here!

Things You Shouldnt Miss in Florence

statues in the front of the uffizi gallery

Florence attracts tons of tourists every year that flock to this beautiful city, thanks to its impressive cultural heritage that offers so many wonderful sightseeing opportunities.

Among the things you should visit in the heart of Florence are the imposing cathedral (the Duomo) with one of the most stunning cupolas in the world, but also smaller churches, like San Lorenzo and Sant Croce, two churches located just a few steps from the center of town. 

Likewise, do not miss the public market, the art galleries, such as the Uffizi and the Accademia, the Ponte Vecchio Bridge, and the gorgeous Piazza Della Signoria, one of the most charming squares in the country.

This 3 day Florence itinerary features some of the highlights you really cannot miss in town, so let’s get started!

If you only have one day in Florence and need an abbreviated itinerary, you can find that here.

3 Day Florence Itinerary: Day One

Start the day at the Duomo, the Santa Maria del Fiore.

the famous belltower and facade of the duomo of florence, also known as the santa maria del fiore cathedral, on a sunny day

If you’ve just arrived in town, no matter what time it is, head directly to the heart of the historic center, Piazza del Duomo, to start your first day exploring Florence.

Your first stop is the fantastic Cathedral of Santa Maria del Fiore (also known as the Duomo), probably the most-visited place in the city, easy to recognize due to its pristine white marble facade.

Santa Maria del Fiore is considered a perfect example of Renaissance art, as well as one of the most remarkable religious buildings in Italy. The construction of the church took about four hundred years to complete — so no wonder it’s so impressive!

Among the most notable features is its famous red-tiled cupola, an architectonic masterpiece created by world-famous Renaissance architect and painter, Filippo Brunelleschi.

On the inner side of the cupola, you can admire a unique series of frescoes of the Last Judgement. 

Check out the other important buildings in the area.

the st john baptistery part of the duomo complex in the heart of florence, a cant miss florence itinerary item

When visiting the cathedral, don’t miss the other two important buildings that stand just meters away, Saint John’s Baptistery and Giotto’s Campanile, all a part of the same religious complex.

Saint John’s Baptistery is, in fact, a minor basilica that features an original octagonal plant and impressive iron gates.

The gates facing the East side were conceived by Michelangelo; they are known as the Gates of Paradise and are well-known for their intricate decorations and unique attention to detail.

Not everybody is aware that the baptistery is one of the oldest constructions in all of Florence, dating back to 1128!

Steps from the cathedral and the baptistery, don’t miss the campanile, locally known as Giotto’s Campanile.

Depicting a completely different style from the cathedral and the baptistery, the campanile was built in perfect Gothic style and it can be easily seen from any point in town!

If you’re not afraid of the heights and are eager to see a different perspective of Florence, then you can climb more than 400 steps that lead you to the top of the tower. These are some of the best views over all of Florence!

Have an espresso in Florences most traditional cafeteria.

espresso and cornetto in a traditional espresso bar

Since visiting Santa Maria del Fiore can take up to about two hours, after the visit is a good time for a short break and a cup of authentic Italian espresso, perhaps with a cornetto if you’re hungry for breakfast! 

If you’re eager to discover Florence’s pace of life, stop for a cup of coffee at Café Scudieri, an elegant cafeteria that first opened its doors back in 1939.

This is the perfect place for coffee and traditional pastries that boasts a spectacular terrace with unique views of the Duomo.

Check out the Piazza della Signoria and Palazzo Vecchio.

the facade and clocktower of the palazzo vecchio in florence italy

Just a short distance from the cathedral, another important Florence landmark is the huge square known as Piazza Della Signoria, a place that hosts several important buildings.

One of them, Palazzo Vecchio, was once the main administrative center in Florence, home to the ruling power of Florence for centuries.

Although everyone knows the place simply as Palazzo Vecchio, its formal name is Palace of the Signoria of the Republic of Florence.

The structure dates back to 1299 and it is constructed like a small castle.

The building is better-known for its important access gate where there is a fantastic replica of Michelangelo’s David (the original masterpiece is in another point in town, Galleria dell’Accademia) as well as a statue of Hercules.

Located on one side of the palace, you can spot a wonderful fountain known as the Fountain of Neptune.

Check out the statues in the Loggia dei Lanzi.

marble statue in the loggia dei lanzi archway in central florence (firenze)

Also in Piazza Della Signoria on the opposite side of the Neptune Fountain, a curious selection of Renaissance sculptures give life to the Loggia Dei Lanzi, also known as the Loggia Della Signoria.

This open-air gallery located adjacent to the piazza features impressive arches and Corinthian columns, and is conveniently located right next to our next stop, the Uffizi Gallery. 

On the steps of the Loggia there are the marble statues of the Medici Lions which were historically the heraldic symbols of the city.

Meanwhile inside the Loggia, other statues include the bronze of Perseus and the head of Medusa and the Rape of the Sabine Women made from a block of white marble — the largest block ever transported to Florence!

Since our next stop, the Uffizi Gallery can take quite a few long hours to explore, pick a bar around Piazza Della Signoria for a quick lunch and move on to the Uffizi.

Spend some time in the Uffizi Gallery.

the famous courtyard that is part of the uffizi gallery a famous gallery in florence italy

The most important art gallery in the city is the worldwide famous Uffizi Gallery which you should book tickets for way in advance to visit if you want to avoid the crowds and even bypass the long lines with a skip-the-line ticket.

This notable art gallery is located a few steps from the Arno River, as soon as you leave the Piazza Della Signoria behind you.

The gallery entirely occupies the first and second floors of the Vasari building, which was built between 1560 and 1580. 

The Uffizi hosts one of the most magnificent art collections in Europe, and certainly the most remarkable Renaissance art exhibition in the world, with masterpieces by artists such as Botticelli, Tiziano, Da Vinci, Raphael, and Caravaggio.

There are also paintings from the 14th century by artists such as Giotto, Piero Della Francesca, Botticelli, Mantegna, Correggio, Leonardo, and Raffaello, in addition to many precious works by German, Dutch and Flemish painters.

Such a massive art exhibition could take days to explore, but if you only want to have a glimpse at the most important works of art, then a guided tour with a licensed guide is the best way to visit.

Book your timed entry ticket or a guided tour online here!

Cross the Ponte Vecchio and spend the rest of the day in Oltrarno.

the covered bridge of the ponte vecchio with several stone arches going over the arno river in florence italy

Our first day in Florence has been packed with visits to interesting sites such as the Duomo and the impressive Uffizi Gallery.

It is a good idea to leave other historic buildings for the following day while devoting the rest of the first afternoon to a relaxing walk in a more tranquil part of town, Oltrarno.

Walk along the river until you reach the spectacular Ponte Vecchio.

Although it is a very crowded place, it’s also an ideal stop for an iconic photo of Florence. Crossing this old stone bridge is certainly part of any Florence itinerary.

The Arno River divides the city in half. It is crossed by numerous medieval bridges, but none of them are as remarkable and famous as Ponte Vecchio (which translates as Old Bridge).

This stone arch bridge hosts dozens of shops built along its whole length!

In the past, butchers, tanners, and farmers occupied the shops, but it currently houses some of the finest art and jewelry shops in town and it is exclusively pedestrian.

Ponte Vecchio leads you to this other side of Florence, where life can take a more relaxed pace and where you won’t find as many tourists.

Depending on how much time available you still have after the Uffizi, you can choose to visit all the premises of Pitti Palace, or devote some time only to its green area, the incredibly beautiful Boboli Gardens.

Check out the Palazzo Pitti and Boboli Gardens.

a gated area in the boboli gardens with greenery and sculptures

Oltrarno is a beautiful area where you can enjoy small eateries, artisan shops with unique souvenirs, and a wonderfully romantic atmosphere.

One of the places that you should check out in the area is Palazzo Pitti and its incredible Boboli Gardens.

Depending on your interests, you can visit both the palace and the gardens, although most tourists just opt for a relaxing walk and skip the palace.

Palazzo Pitti is extremely important to the history of the city. The huge building used to be the home of the important Medici Family, the most important and powerful political dynasty in Florence.

This palace now hosts an important museum complex, with exhibitions and art galleries and endless impressive examples of Renaissance art. If you’re not filled up on art after checking out the Uffizi Gallery, head into the palace museum for even more art!

At the back of the palace, the Boboli Gardens are one of the most interesting places to visit in Florence and make a great change of pace after seeing so much architecture and artwork.

The 16th century Baroque-style gardens are massive, occupying over 45,000 square meters!

The green landscapes are decorated extravagantly, featuring bizarre sculptures, incredible fountains and ponds, and hundreds of plants and trees from all over the world. 

Have dinner by the bridge.

pasta with basil on top and a carafe of red wine with a blurred background of a european city

Finally, head back to the bridge area for dinner.

I have several recommended restaurants in Oltrarno: Cavalieri Ponte Vecchio Ristò, Osteria Ponte Vecchio, and Amici di Ponte Vecchio.

All of them are traditional trattorias offering delicious and time-tested Florentine menus.

Admire the spectacular view from Piazzale Michelangelo.

view over the city of florence at sunset from piazzale michelangelo, a must-stop on this florence itinerary

Finally, walk over to the Piazzale Michelangelo for the most incredible view of the historic district of Florence as seen from a hilltop vista on the other side of the Arno River.

This place is a really popular sunset spot, but it’s also lovely after the sun has set, when all the lights come on in Florence.

There’s also a bronze replica of David here, but you really come for the best views over Florence.

3 Day Florence Itinerary: Day Two

Start the morning at the Galleria dellAccademia to see the Statue of David.

By Commonists – Own work, CC BY-SA 4.0, via Wikimedia Commons

Start your second day with a visit to the Galleria dellAccademia. This is another popular place that often gets packed with tourists, so it is always better to visit early in the day.

The main reason to visit is that the gallery is the place where you can admire the original David sculpture, Michelangelo’s masterpiece.

You’ll need a timed entry ticket to see the Statue of David without the hectic lines, otherwise visiting this attraction can be quite a headache.

In the venue, there are displays of other pieces of Michelangelo’s art, such as test sculptures and even drawings.

The Accademia is also home to a tiny museum of musical instruments and music-related inventions.

Book your timed entry ticket to see the Statue of David and Galleria dell’Accademia here!

Grab something to eat at the Mercato Centrale.

the central market in florence italy

Located near the Galleria dell’Accademia, the Mercato Centrale is one of the most beloved marketplaces in Florence.

You’ll find pastries, sandwiches, and all sorts of other quick bites that will help fuel you up for the rest of this day’s walking tour of Florence.

Check out the charming San Lorenzo and Santa Croce churches.

the cupola in san lorenzo church with fresco painted beautifully

There are many fantastic churches to visit in this beauty other than the Duomo!

San Lorenzo Basilica is one of them. Although it features a structure and architectural style much simpler than the spectacular marble Duomo, this big structure impresses with its imposing dome and terra cotta roof. 

The church was built by the powerful Medici family during the Renaissance, and it is the final resting place of some of the most prominent Medici figures inside the Medici Chapels (Cappelle Medicee).

The church is a great place to admire unique works of art including exquisite examples of funerary art and tombs as well as frescoes and other paintings from the same period.

Another interesting church also in the area of the Duomo is Basilica Santa Croce, which was built around the same time as the Duomo and which shares a few characteristics with Florence’s main church.

Just like Santa Maria delle Grazie, the Church of Santa Croce features a dazzling white marble facade with details in green and pink marble and white stone.

Inside the religious building, you can visit the tombs of some of the most important figures of the Renaissance, such as Michelangelo and Galileo.

Taste the local cuisine.

florentine steak cut to show beautiful rare cooking style

It is not possible to visit Florence and skip the most famous dish in town, the world-famous Fiorentina steak!

Although it can be a fairly expensive experience, the Fiorentina is adelicious meat cut served by the kilo and is worth every single cent you’ll pay for it.

It is often served with some of the local red wines that have made the whole region famous — Supertuscans and Chiantis, both of which are absolutely delicious!

If you’re on a budget and a Fiorentina is out of your league, don’t be discouraged!

The city has other staple dishes that will be equally rewarding: lampredotto is one of them, and can be a good thing to taste if you’re an adventurous eater.

This typical dish of the region is traditionally made from the fourth and final stomach of a cow.

This is then slow-cooked with plenty of herbs in a thick vegetable broth, seasoned with spices, chopped, and served in a hot bun with a variety of sauces or a small portion of fried onions.

Sample a cone of Florentine gelato.

hand holding a chocolate and vanilla two scoop gelato cone

After lunch, take an afternoon break with a delicious taste of gelato!

They say that the modern version of gelato, as we know it today, was created in Florence, so what better place in Italy to sample the country’s favorite afternoon treat?

The story goes that this creamy treat was first produced by the local alchemist Cosimo Ruggieri to please the Medici court back in the 16th century. It seems to have worked — gelato is now everywhere in Italy!

This unique form of ice cream is made using a higher percentage of milk than cream. It is also whipped only for a short amount of time, thus avoiding an excess of air in the gelato.

This, combined with the warmer serving temperature than ice cream, makes its flavor more pronounced and rich!

As expected, there are several gelaterias in town.

They not only serve typical gelati, but also fruit sorbets without any milk, which are both vegan and gluten-free.

Some of the best gelaterie in town are My Sugar close to theAccademia Gallery, Dei Neri, near the Uffizi Gallery, and Vivoli, the oldest gelateria in Florence, dating back from 1929, near Santa Croce church. 

Shop for fine leather products.

various colors of leather bound diaries and journals in a florence street stall

Florence is a perfect Italian destination to purchase refined leather bags, jackets, and shoes!

The region of Tuscany and Florence in particular, are known all over the world for their millennial leather tradition and craftsmanship.

In the area of Santa Croce Church, you will find several artisan leather shops and workshops where you can purchase fine quality leather products at affordable prices, especially considering the level of workmanship.

You can also find them at the outside stalls of the San Lorenzo Market.

These products are some of the best souvenirs from Florence that you can take home with you!

3 Day Florence Itinerary: Day 3 (Tuscany Day Trip)

view of a beautiful tuscan villa with tree lining road in the autumn

As we have mentioned before, you should devote the third day of your Florence itinerary to taking a Tuscany day trip.

Spend the day visiting the amazing vineyards in Tuscany, enjoying the local landscape, tasting delicious wines and learning about the local winemaking tradition.

You can also sample other Florentine delicacies as you move around the magnificent verdant fields of the region — eating well is never a challenge in Italy, after all, and this goes even more so for Florence!

I will suggest a Tuscany itinerary that you can either self-drive or take a guided tour of. If it’s your first time driving in Italy or you plan to drink, a guided tour is the better option.

When planning your day trip to Tuscany, bear in mind that driving in the Tuscan countryside surrounding Florence is not as stressful as it can be to drive in Milan or Rome.

side mirror of a car looking out onto the tuscan countryside

However, since the most important thing you will be doing today is sampling Florentine wines, joining an organized tour is a smart move to avoid the dangers of driving under the influence — as well as expensive fines on the road. 

Remember that drinking and driving are heavily fined in Italy, so having someone else do the driving while you enjoy the delicious Tuscan wines is nothing but the right thing to do.

If you agree with me, I highly recommend checking out this tour,which offers an excellent opportunity to visit some of the highlights in the region and to taste some of the most delicious Tuscan wines!

Book a guided tour bringing you on a day trip to Tuscany here!

First Stop: Siena

the beautiful hillside city of siena in the tuscany region

The best way to start the day is to head directly to Siena, an important medieval city in Italy where you can spend some time walking in the old district where a myriad of ancient terracotta roofs adds a pop of color to the whole landscape.

In Siena, take some time to discover the Cathedral of Siena (Duomo di Siena). The medieval church was built between 1215 and 1263 featuring an imposing dome and a bell tower. 

The dome, completed in 1264, has a famous lantern made by the artist Bernini. Inside the bell tower, there are some iron bells, the oldest of which dates back to 1149.

Some of the finest Italian artists of those times completed works in the black and white cathedral, which proudly features the colors of the city!

Second Stop: San Gimignano

the beautiful low hill town of san gimignano with the towers that it is famous for in tuscany

Located atop a low hill, San Gimignano is one of the most representative Tuscan towns dating back to the Middle Ages.

It’s home to some unique tower houses from that same period which have earned this town the status of being a UNESCO World Heritage Site.

In San Gimignano, you can take some time to visit its traditional squares and ancient palaces, as well as the famous medieval skyscrapers.

The town hosts about a dozen of these tower houses as well as protective encircling walls, that shelter incredible churches and public buildings constructed both in Romanesque and Gothic styles.

When in San Gimignano, it is a good idea to taste its distinctive white wine, the Vernaccia di San Gimignano, which is produced from the Vernaccia grape variety, an ancient grape that is grown on the sandstone hillsides of the town!

Before heading to the last stop of this day trip, you can make a stop to explore a local wine state in the world-famous Chianti wine region.

Most wineries in the area offer wine tasting sessions paired with an informal lunch. This gives you the chance to sample some authentic farmhouse dishes that are so beloved in Tuscan cuisine.

Last Stop: Pisa

leaning tower of pisa and the church of pisa

Fairly close to Florence, it is only fair to end this day trip to the Tuscany region by visiting Pisa and, of course, the fantastic Leaning Tower of Pisa located in the heart of Piazza dei Miracoli. 

Here, it is also a good idea to spend some time exploring the Cathedral of Pisa, devoted to the Assumption of the Virgin Mary, not far from the Pisa Baptistry and Leaning Tower, which is — in fact — the campanile of this basilica.

The cathedral was built in the so-called Pisan Romanesque Architecture and it was completed in 1092, making it one of the older cathedrals in Italy.

Where to Go After Florence & Tuscany

If you have time to extend your trip, it’s quite easy, as Florence enjoys such a central location in Italy.

You can add on a few days in Rome before heading down to Naples and the Amalfi Coast, or you can go a bit off the beaten path to explore some of the charming towns of Umbria that are less-visited.

Alternately, you can head north to Milan, the Cinque Terre, and the Liguria region of Italy.

7 Best Tuscany Wine Tours from Florence: A Curated List

view of wine regions of florence's surrounding area of tuscany

If you’ve been planning your Italy trip for a while now or if you’re really into Italian food and wine, you’ve almost certainly heard about Tuscany and the impressive varieties of wines produced in the area.

Considered among the best wines in the world, Tuscany is a heavy-hitter in the world of Italian wines.

When spending time in Florence, do not miss the chance to try a sip (or thirty!) of the local vintages.

But planning a Tuscany wine tour on your own can be confusing.

For one, their websites aren’t exactly the most user-friendly, and language barriers when making calls to reserve tastings can be an issue.

For another, there are so many wineries spread out across such a wide region that it can be impossible to do without a car (which then begs the question — who has to drive?)

View of a road in Tuscany overlooking a vineyard

While you can certainly dedicate several days to exploring Tuscany (like I’ve outlined in this 5 day Tuscany itinerary), not everyone has that time in their schedule.

If time is short, going on a wine tour from Florence can be one of the better ways to explore the wine scene of Tuscany — and leave that car rental behind, so you can have a designated driver along the way, of course!

Here are some of the best Tuscan wine tours from Florence that are worth your time.

So be sure to save a day of your Florence itinerary pulling yourself away from its many museums, churches, and landmarks as you get to know its wine and gastronomy!

This is one of the best Florence day trips you can do, so make sure you save time for it.

If you want to experience both Florence and Tuscany, I suggest doing a day trip of the wineries from Florence, then chilling out in the Tuscan countryside and visiting some of its towns — perhaps staying in a pool villa like one of these ones!

This post was written by Gabi Ancarola, a travel blogger who lived in Italy for 10 years before moving to the island of Crete. In addition to blogging, Gabi is a licensed tour guide who organizes food and wine tours as well as sightseeing excursions. Enjoy her knowledge of Tuscany as well as her wine expertise here! This post was updated on September 15, 2023 to ensure all the tours are active.

Our Top 3 Picks for Tuscany Wine Tours from Florence

#1 TOP PICK

Two glasses of wine overlooking fields and vineyards in Tuscany

⭐️⭐️⭐️⭐️⭐️
Tuscany Wine & Food Tour with Guide
✔️ Three traditional Tuscan wineries
✔️ Authentic Tuscan lunch plus olive oil and balsamic tastings

↳ Book it

#2 PICK

backroads of tuscany in a small cute car

Vintage Fiat Tuscan Winery Tour
✔️ Get driven through Tuscan backroads in a vintage Fiat 500
✔️ One winery visit with tasting, Tuscan lunch, and olive oil tastings

↳ Book it

#3 PICK

vineyards in tuscany with a winery house on the hill

Chianti Wineries Tour
✔️ Two wineries in Chianti
✔️ Snacks of cheese, bread, salumi, and olive oil

↳ Book it

 Wines of Tuscany

Two wine barrels on the hill in Tuscany, a popular place to go on a wine tour from Florence

 Before we get into all the best wine tours from Florence, let’s brush up a bit on the wines you can expect to see on a trip through Tuscany.

Here’s a quick glimpse into some of local varietals and historical background that define Florence’s refined wine panorama.

 As you may have already read about in my article about Florence, the city has a long, remarkable history spanning from the Roman Empire well into modern times.

Vineyards were planted in the region as far back as Ancient Roman times.

However, it was during the Middle Ages and the Renaissance, in the surrounding fields of Florence (what today is the region of Tuscan wine country), that winemaking became a solid and storied tradition.

As years went by, it eventually evolved into a prestigious industry and a trademark of the region.

Florence was not only the cradle of the Renaissance with its plethora of churches, palaces, and culturally significant paintings and sculptures.

It was also the birthplace of the noble Sangiovese grape, one of the most famous varietals in Italy.

Blueish purple Sangiovese grapes seen on a pallet in Italy

The Sangiovese grape has grown for centuries on the lush rolling hills of the region, populated by hundreds of vineyards and olive groves.

There are several wine areas in Tuscany. The most famous of all is Chianti, also classified as the oldest wine region in the world.

Some other important wines you will be able to try in the area are the magnificent Chianti Classico, the Nobile di Montepulciano, and the Brunello di Montalcino.

You can also learn all about the Super-Tuscan wines while sipping your way through the scenic local vineyards.

It’s a bit of a crash course in wine education, with thankfully no test at the end.. though you will likely crash after your wine tasting tour!

Chianti Region

Rows of vineyards and fields in the Chianti region of Italy with a winery situated in the middle of it on a summery day

 Arguably the most important, famous, and remarkable wine region in the country, the boundaries of Chianti were defined back in the 16th century by the Grand Duke of Tuscany.

 Amongst its beautiful green hills, dozens of vineyards give life to Sangiovese, a grape variety that offers all the favorite characteristics of a red wine: boldness, fruitiness, and structured tannins.

Head here to visit several important wineries, taste a glass or two of the spectacular Chianti Classico, and be amazed at the gorgeous views and soft magical light of this quaint area.

You simply can’t miss doing a Chianti wine tour while you’re in the region. 

Montepulciano

Rows upon rows of vineyards, trees, and wineries in the hills of Montepulciano region of Tuscany

 Known for its Nobile di Montepulciano (which should not be confused with Montepulciano d’Abruzzo, a well-known wine from another Italian region), Montepulciano is a red DOC wine.

It is not a single varietal but rather a blend. It is primarily made from Sangiovese grapes blended with Canaiolo Nero and other grape varieties.

This full potential of this wine benefits from at least one year in a barrel and a total of two aging years (three aging years make it a Riserva wine). 

Montalcino

Rows of grapes in a vineyard with a stone wine house nearby in the area of Montalcino, Italy in Tuscan wine region.

Moving along towards the province of Siena, Montalcino is a beautiful medieval hill town as well as another impressive wine region of Italy. 

Montalcino is the place where one of Tuscany’s best aging wines, Brunello di Montalcino, is made. It typically requires a minimum of two years in a barrel. 

The Super Tuscans

A Super Tuscan wine being poured into a clear wine glass

Although Chianti is usually the first wine that comes to mind when thinking about Tuscany, the area has been growing a name and reputation for a different type of wine… one that wasn’t always so respected, known as the Super Tuscans. 

But what even is a Super Tuscan?

A Super Tuscan is a style of wine more fruity and powerful than Chianti.

It blends popular international grape varieties, such as Cabernet Sauvignon or Merlot, with local varietals like Sangiovese.

The result is a wine with lower acidity while maintaining French oak flavors (vs. Chianti, which requires aging in Slovenian oak casks) and robust tannins. 

These slightly rebellious wines (considered DOC rule-breakers), are now known as part of the category IGT (which can be roughly translated as Typical Geographic Indication).

They have become a prestigious category of their own, often competing with renowned Italian varietals and even wines from prestigious French vineyards!

Independent Wine Tasting or Wine Tours from Florence?

View of vineyards and a winery as seen from a vantage point further away with Tuscan hills in the background

 It’s hard to go wrong renting a car in Tuscany and driving your way through the inspiring Tuscany hills — you’ll undoubtedly get lost once or twice, not that you’ll mind with the views.

However, you won’t always have enough time to visit many places on your own, and – more importantly – drinking and driving are heavily fined in Italy, for good reason.

 The best piece of advice that I can give you is to join one of the many wine tours, which allows you to visit multiple wineries and old towns in a single day on one of these easy Tuscany wine tours from Florence.

A guided tour may not sound as romantic as zipping from winery to winery on the back of a Vespa or in your own little Fiat… but it’s easier, more convenient, and a lot safer.

This way, you’ll be able to taste as many wines as you want without being unsafe when it comes to driving back to your hotel when the day is over… or making an unlucky person in your travel party the designated driver! 

Pro Tip: If you do decide to rent a car in Tuscany and have a designated driver plan in place, I suggest booking your rental car through Discover Cars — they search over 500 car rental companies, including smaller local ones, to find the best price for your rental!

Best Wine Tours from Florence

Two empty wine glasses overlooking rows of grapes on a vineyard in Tuscany

According to your taste, your budget, and the available time you have, you can choose whatever tour from Florence best suits your style.

You’ll find everything from full-day tours with a visit to a medieval town, brief sampling tours, vineyard tours, and even tours with visits to two or three wineries in a day with a three-course meal included! 

All these Tuscan wine tours include pick up, drop-off, a tour guide to teach you all about the wines of Tuscany, and of course… samples of several different wines included!

  • Best Budget Wine Tour: Chianti Wineries Tour with Food & Wine Tasting from Florence is a half-day experience that takes you to two wineries in the Chianti Hills. 

    During the trip, you will meet local winemakers, walk through stunning vineyards, and sample local wines and other gastronomic goodies such as cheese, olive oil, and balsamic vinegar.

Book your Chianti wine tour here!

A bottle of Chianti on a barrel with an empty wine glass overlooking the rest of Tuscan countryside
  • Best Small Group Tour: Tuscany Wine & Food Tour with Guide from Florence is an intimate experience that takes you to visit three wine estates and their wine cellars and taste several wines as well as local olive oil and high quality balsamic vinegar. 

    After, you will enjoy a fresh lunch of authentic Tuscan specialties and visit not only the idyllic Tuscan hills and vineyards, but also lesser-known Tuscan villages.

Book your small group tour here!

small taste of red wine standing on the table, blurry vineyard behind it
  • Best Wine Tour for Younger Travelers: Tuscany Wine Tasting Full-Day Trip from Florence is a full-day wine tour to the Tuscan countryside, open to all ages but particularly geared toward independent travelers aged 18-35. 

    During the day you can socialize with other travelers while exploring the beautiful Chianti landscape and sampling delicious traditional wines.

     This is a fun experience, with stops at the medieval walled hill town of San Gimignano as well as a wine tasting school to learn how to recognize different flavors and develop your palate so you can be the wine snob you’ve always wanted to be!

Book your guided tour of Tuscany’s wines here! 

scenery of a Tuscan hill town outside of san Gimignano as well as wineries and vineyards
  • Most Scenic Tour of Tuscany: Wine Tasting and Tuscan Lunch in a Vintage Fiat 500 is a perfect experience for Instagram fans eager to surprise their followers with amazing vintage photos, but it’s also perfect if you just love old-school cars and wine! 

    On this half-day tour you’ll join a colorful convoy of vintage cars winding through Florence and rural Tuscany, and head to a fifteenth-century villa and vineyard for fine wine and an olive oil tasting paired with a lunch of Italian delicacies. It’s a unique experience you won’t forget!

Book your Fiat tour of Tuscan wineries here!

red vintage fiat next to a door in Tuscany italy
  • Best Evening Tour with Dinner: Wine Tasting and Dinner in the Vineyards of Chianti is a trip that lets you get lost in a romantic setting right during sunset, soaking in some of the most unforgettable scenes of your Italian experience.

    The excursion includes a wine tasting in a winery, a visit to the farm’s historic chapel, and ends with a memorable Tuscan dinner in the vineyards.

Book your evening wine tour with dinner here!

sunset over a vineyard in Tuscany italy for a romantic tasting and dinner experience
  • Best Tour Combining History and Sights: Chianti and Castles Tour with Wine Tastings does not depart from Florence, but rather from Siena, a city that you can easily reach from Florence by train or bus.

    I’ve decided to include this tour even with its different departure point as it is a real value-for-money experience. 

    The tour starts with the opportunity to explore the gardens of the Brolio Castle and visit the Castellina in Chianti.

    Next up, you will go for a wine tasting experience at a wine estate that includes Chianti and Super Tuscan wines, all paired with a delicious meal of typical Tuscan food. You will also visit ancient churches and small villages where the rhythm of life has remained unchanged over time.

    Finally, you will visit another winery in the middle of the Chianti Classico area, where you’ll have a second optional wine tasting as well as an extra virgin olive oil tasting.

Book your castles and winery tour here!

the remnants of brolio castle in Tuscany and the vineyards surrounding it which you can visit on a wine tour in Tuscany
  • Best Wine Tasting Safari: Chianti Wine & Food Safari is a 10-hour Tuscany wine tour that combines adventure and delicious Tuscan wines. Buckle up for this unique comprehensive introduction to the region and its wines while touring two of its best wine estates.

    Sample the winery’s signature wines and receive tips about the art of wine tasting and pairing wine with food. Tastings also include the sampling of cheese and olive oil. 

    Here’s the safari part: you’ll actually go off-roading through ancient woodland and rolling hills dotted with rustic farms and churches as you make your way to a typical Tuscan restaurant with stunning views. 

    To visit the final wine estate, you go even deeper into the Chianti hills while enjoying the incredible countryside on your way to a Chianti Classico vineyard.

    The final stop is in the village of Greve, where you will have free time to wind down, have an espresso or simply wander the traditional alleyways.

Book your wine tasting safari here!

Wine Tasting in Florence

hands holding wine glasses with a plate of cheese and dried fruit behind the people

 If you have limited time in Florence and are not able to visit the rural Tuscany region, it does not mean you cannot taste the local wines.

The city is full of gorgeous bars, wine shops, and enoteche (wine bars) where tasting Tuscan wines is super easy.

Head to one of the many wine bars in the center of Florence to sample some good Tuscan varieties.

Here are some of the best-known wine bars where you can enjoy wine tasting without leaving the city:

Le Volpi e LUva: This is a very famous wine bar in Florence, also serving stunning local dishes. They have a good choice of Tuscan wines on their wine list, available by the glass or by the bottle. If you have no idea what to taste, ask the sommelier for a suggestion! The staff is approachable and knowledgeable and will offer sensible advice.

Enoteca Marconcini: If you’re visiting the Marketplace area, then head to this enoteca for an impeccable local wine experience. Do not be deceived by its tiny size – this place features an extensive wine list. You can also indulge in local charcuterie and cheese during your tasting.

Pitti Gola e Cantina: Another picturesque wine shop right opposite Pitti Palace, in the Oltrarno district. Here you can taste wine by the glass and purchase a bottle to take back home with you. If you’re looking for a complete experience, check out their wine tasting combined with a lunch menu.

While you’re exploring, don’t forget to sample some of the other delicious products that Tuscany is known for, including extra virgin olive oil and balsamic vinegar.

You’ll find the local varieties on display throughout most of Florence’s shops and restaurants!

Italian Wine Words to Remember

glass of wine with tuscan countryside in the background

 There are a few Italian wine-related words that you’ll often hear during the tours even when they are conducted in English.

These words help to define the wines you will taste and the land you will visit.

So keep them at the ready in your mind and impress yourself, if no one else!

Vino bianco: white wine

Vino rosso: red wine

Vino rosato: rose wine

Dolce: sweet

Secco: dry

Vino amabile: semisweet

Vino frizzante: slightly sparkling wine, fizzy

Spumante: sparkling wine

Riserva: a wine aged longer than usual 

Bollicine: bubbles

Cantina: both the cellar and the winery

Azienda vinicola: wine estate

Vigna: vineyard

Annata: vintage year

Calice: wine glass (also known as bicchiere, a plain glass)

Cavatappi: corkscrew or bottle opener

Bottiglia: bottle

Etichetta: label

Tappo: cork, closure, cork cap

Sughero: cork, the material

Degustazione: tasting

Salute/chin chin: cheers! 

Are you ready for a tasty wine tour in Florence? You won’t regret a drop of it!

Siena Itinerary: 2 Days to Discover the Medieval Tuscan City

the famous exterior of the siena duomo

If your travels happen to bring you to Tuscany, don’t just stick to Florence!

As you explore, you’ll soon see that Siena is a beautiful city worth adding to your Tuscany itinerary

⌛ Planning your Siena trip in a hurry? Here are my quick picks.

🏛️ Best Siena Tours & Experiences
1. Siena Cathedral Opa Si Pass or Guided Tour (#1 attraction!)
2. Full-Day San Gimignano and Montalcino Wine Tour (best wine-focused day trip)
3. Siena Lunchtime Food Tour (top choice for foodies)

🛏️ Best Siena Hotels
1. Hotel Certosa di Maggiano (converted monastery, now a luxury hotel with pool)
2. Palazzetto Rosso Art Hotel (historic palazzo, now an eclectic boutique hotel)
3. La Villa (B&B style lodgings in a renovated 19th century villa)

🚘 Planning to travel around Tuscany independently after? Look into car rentals in Siena.

This medieval Tuscan city south of Florence is surrounded by scenic countryside landscapes and vineyards, making it the perfect destination for both culinary and cultural exploration.

While many visitors will simply travel to Siena on a day trip, spending a couple of days in the city is a fantastically rewarding experience. 

With the extra time on your side, you can visit beautiful landmarks, check out the museums, sample delicious Tuscan food, and maybe even join a wine tour!

Street scene in Siena with brick buildings and more modern buildings too

I traveled to Siena while living in Italy, and I was truly amazed by the stunning medieval architecture, the imposing Piazza del Campo, and the beautiful Duomo. 

This two-day Siena itinerary is perfect if you want to visit the city’s main attractions, enjoy great food at Tuscan restaurants, and explore the surrounding countryside.

Getting to Siena

Train schedule in Italy with some routes heading to Siena

There are a few ways to get to Siena, depending on where you’re starting from.

Most people will either take a train to Florence or fly into the airport in Florence first before visiting Siena.

From Florence, the train to Siena takes about 1.5 hours via fast train. You can book train tickets via Omio to get a better price in advance.

Florence Airport is also a good place to pick up your car rental if you’re planning on road tripping through Tuscany.

If you’re renting a car during your time in Siena, I recommend looking for the best rental car deals on Discover Cars.

They search over 500 agencies (including small local ones other car rental search engines skip over) and make pricing clear and easy, with no bait and switches.

Check rental car prices from Florence here!

Taxis from Florence Airport are possible, but expensive — around 190 Euros. If you go that rote, I recommend booking an airport transfer through Welcome Pickups.

Day 1 of Your Siena Itinerary: Siena’s Main Landmarks

Explore Siena’s historical center.

Sunny day in Siena, Piazza del Campo with the Pubblico palace and Mangia tower, two of the most famous spots on a Siena itinerary besides the Duomo
The medieval Piazza del Campo, one of the most notable piazzi in Italy

Begin your day by exploring Siena’s historical center with its iconic squares and landmarks.

You can fuel up with a delicious breakfast at one of the many bars in the city center, like Torrefazione Fiorella or Caffè 19zero3.

Ready to start seeing the sights? It’s time to admire one of Italy’s most iconic squares, Piazza del Campo

The wide, shell-shaped square is among Europe’s most notable medieval squares.

It’s surrounded by beautiful and well-preserved medieval buildings, from the iconic Torre del Mangia to several noble buildings.

Close up on the ancient tower, torre del mangia, in Siena city center
The famous Torre del Mangia

Piazza del Campo famously hosts the twice-annual historical horse race, Palio di Siena

The racers represent ten of the 17 contrade or city wards of Siena, each wearing the colors of their ward.

The Palio takes place on July 2nd and August 16th, so plan accordingly if you want to witness this unforgettable event.

Be sure to take some time to wander around Piazza del Campo and explore the nearby streets, checking out Siena’s beautiful architecture. 

Detailed view of the marble fountain called Fonte Gaia (which is Italian for Fountain of Joy), part of Piazza del Campo in Siena
The aptly-named ‘Fountain of Joy’ of Fonte Gaia

Admire the iconic Palazzo Pubblico with its imposing tower and the beautiful Fonte Gaia.

While you’re in the area, stop by the 15th-century arcade Loggia del Papa erected by Pope Pius II, and check out the decorated arches at Loggia della Mercanzia.

The elegant Loggia della Mercanzia, with arches that are decorated with ornate detail and high ceilings
The arches of Loggia della Mercanzia

If you’re up for a bit of a walk, you can explore more of the historical center and check out Siena’s old city gates. 

Each gate is just a 10-15 minute walk from Piazza del Campo. If you ask me, Porta Camollia, Porta Ovile, and Porta Pispini are the most beautiful gates. 

Enjoy the view from Torre del Mangia.

Aerial view of the Piazza del Campo from above
Enjoy dizzying views from the Torre del Mangia

While in Piazza del Campo, you shouldn’t miss climbing the Torre del Mangia to enjoy a panoramic view of Siena.

The 87-meter-tall tower dates all the way back to the early 14th century and is part of the Palazzo Pubblico, the former seat of the Republic of Siena’s government.

The height of the Mangia Tower is the same as the cathedral’s bell tower, a cunning design decision intended to symbolize the equal importance of the church and the government.

Technically, the church bell tower is actually only 77 meters high, but it sits in a higher position on the hill, so both towers reach the same height.

Aerial view of the Piazza del Campo, Siena seen from the panorama at Torre del Mangia.

The tower’s name, Mangia, comes from the first bellringer, whose nickname was Mangiaguadagni (Italian for “profit eater”) or simply Mangia for recklessly spending his money.

In 1360, he was replaced by a mechanical clock, but locals kept calling the tower Torre del Mangia.

You can visit the tower daily from 10 AM, but closing hours vary with the seasons.

Visits are scheduled in 45-minute shifts, so you may want to buy your tickets in advance since you may not find slots right when you arrive. Tickets are 10€.

Visit the Duomo di Siena. 

Siena Cathedral with its black and white striped tower and pink-hued marble facade with ornate marble work and paintings against a bright blue sky in Siena, Italy
The famous Siena Cathedral or Duomo in Italian

Another must-see landmark in Siena is the cathedral, or Duomo di Siena.

The monumental complex of the cathedral includes the Duomo, the Piccolomini Library, the Panorama and New Cathedral, the Crypt, the Baptistry of San Giovanni Battista, the Oratory of San Bernardino, and the Museo dell’Opera.  

The Duomo di Siena, or Cathedral of Santa Maria Assunta, is among Italy’s most significant cathedrals, featuring Romanesque and Gothic architectural elements.

The striped interior of the Siena cathedral with a starry ceiling and stained glass and arches and domes and beautiful inlays
The interior of the Siena Cathedral

The 13th-century cathedral is known for its rich decorations, along with the iconic striped façade and bell tower.

The cathedral is home to several masterpieces, ranging from Pinturicchio’s paintings to sculptures by Donatello, Michelangelo, and Bernini.

However, the cathedral interior’s most distinctive feature is the graffito and mosaic marble inlay floor.

The Piccolomini Library, dedicated to Pope Pius II (formerly known as Aeneas Silvius Piccolomini), features a cycle of colorful frescoes by Pinturicchio illustrating episodes from the pope’s life.

The ceiling of Siena Cathedral's ornate gold inlay and fresco work of the Piccolomini Library on full display
The ceiling of the Piccolomini Library

The frescoes, painted between 1503 and 1508 in grotesque style, are incredibly vivid and well-preserved.

The Panorama is a stunning viewpoint on top of what was originally intended to be the façade of the New Cathedral.

Projects to expand the Siena Cathedral began in the early 14th century but were later abandoned due to the Black Death, the infamous bubonic plague epidemic that decimated Siena’s population in 1348.

The Unfinished Façade, also known as Facciatone, was kept standing alongside a few walls.  Today, you can now walk on top of the Unfinished Façade for a stunning view of Siena’s historical center.

Facciatone or the unfinished facade, where you can get a good view of Siena, now an open theater-style facade
The Facciatone from below – from above, you get great city views!

In case you’re looking for even more magnificent art, there’s plenty more to admire.

The cathedral’s Crypt houses beautiful 13th-century frescoes by Sienese artists.

Additionally, the Baptistry of San Giovanni Battista houses 15th-century frescoes, while also having a stunning building and facade.

Facade of the Bapistry Cathedral in Siena, with ornate white striped marble and gold roof with circular window
Exterior of the Baptistry of San Giovanni Battista

As well, the Oratory of San Bernardino displays Sienese paintings from the 13th to the 18th centuries.

Last, but certainly not least, the Cathedral Museum houses a collection of statues from the cathedral façade.

It features a 14th-century altarpiece, several paintings, and other objects and decorative elements from the Duomo di Siena.

Duomo di Siena Ticket Options

The facade of the Santa Maria Cathedral in Siena, the Duomo by other name. There are triangular pieces with paintings and lots of spires and marblework.

You can buy a ticket that includes just the Duomo for about $10 or one that includes access to all the structures of the cathedral’s monumental complex for about $19 USD with the Opa Si Pass.

The cathedral’s floor remains covered most of the time, except for brief periods when it is revealed to allow visitors to see the stunning decorations.

You can buy skip-the-line tickets online here (or here if you want the full Opa Si pass that includes all the sights).

roof view of the siena interior cathedral duomo view with gold gilded detailing and lots of stars and navy backdrop

Furthermore, you can add on Gate of Heaven tickets to access a series of rooms and areas just below the cathedral’s roof, offering stunning panoramic views of the cathedral’s interior and exterior.

That costs an extra fee and isn’t incldued in the ticket price.

You can buy all ticket types for the cathedral complex online. Alternatively, you can book this 2-hour Siena tour which includes a guided walking tour of the city center and skip-the-line tickets for the Duomo.

The cathedral visit can take several hours, so you may want to split it between the morning and afternoon.

However, tickets are valid for three consecutive days, so you could even leave some areas for your second day in Siena.

Have a traditional Tuscan lunch.

Typical small cafe in Tuscany, Italy, with blue table clothes and green sunflower cushions on the seats, with a cute chalkboard
Typical al fresco dining in Siena

After exploring the Duomo di Siena, or part of it, it’s time for a lunch break.

Thankfully, Siena offers a variety of traditional restaurants where you can sample tasty Tuscan dishes and local wines. 

Osteria degli Svitati and Osteria Il Carroccio are both great options, serving delicious pasta and traditional meat dishes.

Visit more landmarks in Siena.

Monument to Sallustio Bandini and yellow-hued building of Palazzo Spannocchi in the famous Piazza Salimbeni, part of Siena key landmarks.
Monument to Sallustio Bandini and Palazzo Spannocchi in Piazza Salimbeni

Spend the afternoon visiting more landmarks in Siena’s historical center.

You can check out more structures of the cathedral’s monumental complex or discover other historical buildings.

Palazzo Salimbeni is a 14th-century Gothic palace that houses the Banca Monte dei Paschi di Siena, the world’s oldest bank. 

Two other historical palaces, Palazzo Tantucci and Palazzo Spannocchi, enclose Salimbeni Square, one of the most iconic in Siena.

Yellow facade of the building called Palazzo Spannocchi which is part of Piazza Salimbeni in the Siena historical center, a must visit on a Siena itinerary
Detail of Palazzo Spannocchi

At its center is the statue of Sallustio Bandini, a Sienese politician and economist.

Another structure worth visiting is the Fontebranda, a 13th-century fountain featuring Gothic arches providing access to the interior. 

The fountain is famously mentioned by Dante Alighieri in his Divine Comedy. The tank is fed by water through underground canals from outside of Siena.

The view from the side profile of San Domenico church, an important landmark in the Tuscan city of Siena, Italy, on a summery day with no clouds in the sky.
The San Domenico Basilica

Lastly, visit the Basilica Cateriniana di San Domenico, one of Siena’s most important churches. 

The church is dedicated to Saint Catherine of Siena, Italy’s patron saint together with St. Francis of Assisi and a co-patron saint of Europe.

The church is a national monument and houses several relics of St. Catherine of Siena, including her mummified head (yup, really!)

Enjoy the sunset from Fortezza Medicea.

View of the famous cathedral of Siena (Duomo) as seen from the Medici Fortress with a rainbow over the city
Views from the Medici Fortress

As the day comes to an end, head to the Medici Fortress for a pleasant stroll and to enjoy stunning views of Siena. 

You can walk around the fortress walls and then head to the nearby viewpoint, Vista Panoramica di Siena, for a sweeping sunset view of the city, with the Duomo and the Mangia Tower dominating the skyline.

Have dinner and stroll around Siena at night.

Lit up view of Palazzo Publica and Piazza del Campo through an arch with a midnight blue sky in Siena at night
View of Palazzo Publica and Piazza del Campo

End your day with a walk back to Siena’s old town for dinner and a peaceful stroll around the charming city at night.

Check out to La Taverna di San Giuseppe for refined Tuscan dishes in a charming setting inside an ancient Etruscan cellar, or head to Pizzeria Alle Scalette for delicious pizza.

After dinner, you can enjoy a pleasant walk with fewer crowds or stop for a glass of wine or a cocktail.

Trefilari Wine Bar is a great spot for wine tasting, while Caffè Le Logge is perfect for cocktails.

Day 2 of Your Siena Itinerary: Wine Tours and Museums

Old medieval streets of Siena, with arches, cobblestone, and beautiful architecture

For your second day in Siena, you have two options.

First, you can join a full-day tour of the countryside to visit a few picturesque villages while sampling local wines.

Alternately, you can divide your day in two, half to visit other sights in Siena and the other half for a short wine tour.

If you choose to join a full-day tour, here are some great options.

Option One: Full-Day Pienza and Montepulciano Wine Tour

The charming hillside town of Pienza with stone walls, stone architecture, church steeples, cypress trees
The beautiful Pienza

This 8-hour Tuscan wine tour will guide you along picturesque countryside roads to the charming towns of Pienza and Montepulciano. 

From Siena, you’ll first head to Pienza, a town commissioned by Pope Pius II, who wanted to renovate his hometown.

After exploring the lovely medieval Pienza, you’ll have a delicious lunch at a delightful local farm, where you can also learn about pecorino cheese making.

After lunch, you’ll visit Montepulciano, one of Tuscany’s most famous hilltop towns, famous for the wine of the same name produced locally.

You’ll tour one of the wineries and stroll around town on your own. 

After the tour, you’ll get back to Siena in the late afternoon.

Option Two: Full-Day San Gimignano and Montalcino Wine Tour

view of the city of san Gimignano with its medieval stone towers protruding from the rest of the skyline of the hillside town
San Gimignano and its famous towers

This small group wine and Tuscany tour lasts roughly 11 hours, so be prepared for a packed itinerary. 

First, you’ll visit the beautiful town of San Gimignano, known for its many medieval towers.

After getting a few tips and useful info from your guide, you’ll  have some free time to explore the town by yourself.

Following San Gimignano, you’ll head off for lunch and wine tasting at a farm in the Chianti region, famous for Chianti wine production.

You’ll sample local products and taste delicious wine before driving around the beautiful Val d’Orcia, another popular wine region.

In the afternoon, you’ll visit the hilltop town of Montalcino, where you can shop for exclusive Brunello di Montalcino wines.

Be sure to save some room, since you’ll have another Tuscan wine tasting and sample more Tuscan food before heading back to Siena in the evening.

Option Three: Full-Day Brunello di Montalcino Guided Wine Tour

the hilltop town of montalcino in tuscany cascading down the hillside with stone structures and green trees
The lovely Montalcino, a winemaking town in Tuscany

This 9-hour wine tour focuses on the Montalcino wine hill.

After a scenic drive through the beautiful rolling hills of the Tuscan countryside, you’ll reach Montalcino to learn how the local wine, Brunello di Montalcino, is made and have a tasty traditional lunch at a family-run winery.

You’ll have time to explore Montalcino, visit its medieval fortress, and go shopping for local products and wines.

In the afternoon, you’ll visit the ancient Benedictine Abbey of Sant’Antimo, a Romanesque abbey set in the peaceful countryside south of Montalcino.

Lastly, you’ll get to visit another winery to learn more about wine production and the aging process and visit the cellars.

After the last wine tasting, you’ll be driven back to Siena.

Alternately: First, visit one of the city’s many museums 

The exterior of the museum that is now housed in Ospedale di Santa Maria della Scala, which was a medieval hospital
The museum at Santa Maria della Scala

If you want to spend more time in Siena visiting one or more museums, you can do so in the morning. 

First, take the chance to visit any areas of the cathedral complex you didn’t get to see on the first day.

Then, head to another museum, like Santa Maria della Scala or the Pinacoteca Nazionale di Siena.

Santa Maria della Scala used to be a hospital, one of the first in Europe, dedicated mainly to caring for abandoned children, pilgrims, and the poor.

The hospital’s name refers to its position facing the steps leading to the cathedral (la Scala).

In 1995, the Hospital, as it is still commonly called, was reopened as a museum. 

Santa Maria della Scala houses the National Archaeological Museum, the Piccolomini Spannocchi paintings collection, and the Fonte Gaia.

This is an epic 15th-century marble layout of Jacopo della Quercia’s fountain that used to be in Piazza del Campo, later replaced by a Carrara marble copy.

The art gallery called the Pinacoteca nazionale in Siena, with view of the facade
The art gallery, Pinacoteca Nazionale di Siena

The Pinacoteca Nazionale di Siena, on the other hand, is an art gallery housing masterpieces by Sienese artists ranging from the late medieval era to the Renaissance.

The small gallery is less popular than other tourist attractions in Siena, so you can take some time to admire the paintings without crowds.

Next: join a short wine-tasting tour

Two glasses of wine overlooking fields and vineyards in Tuscany
Wine tasting in Tuscany is a must on any Siena itinerary!

No trip to a Tuscan city would be complete without some wine tasting. These shorter tours are ideal if you don’t want to spend the entire day out. 

The first two activities include food too, so they are great alternatives to a typical lunch.

Option One: Half-Day Educational Wine Tour and Tasting

sampling different florence tuscan wines
One option for wine tasting near Siena

This short wine tour takes place in an organic winery on the outskirts of Siena.

After visiting the vineyards, you’ll check out the cellars to learn about the process of winemaking and taste four different organic wines, followed by a light lunch with Tuscan specialties.  

Option Two: Walking Food Tour with Tastings

different meats and salamis and cold cuts from italy arranged on a tray during a food tour in siena
A selection of antipasti on a food tour in Siena

If you want to stay in the heart of Siena and combine lunch with a guided walking tour, this is the perfect activity for you!

Your guide will take you to at least four eateries where you’ll learn about the dishes you will try and the local culture.  

Option Three: Chianti and Castles Tour

hand holding a glass of chianti wine
Chianti is a must while in Tuscany!

This is a longer activity starting right after lunch that allows you to explore the Chianti region and sample delicious wines at local wineries. 

The five-hour tour includes two stops at Chianti wineries, one wine tasting, and an olive oil tasting.

Plus, you’ll drive through the scenic Tuscan countryside, passing medieval castles and small villages.

If you have time: Visit Santuario Casa di Santa Caterina and/or Basilica di San Francesco

St Catherine sanctuary and Basilica of San Domenico in Siena
The Saint Catherine Sanctuary

If you have extra time in the afternoon, you can visit one or two more churches.

It should come as no surprise that Italian cities are renowned for their beautiful churches, and Siena is no exception.

The Shrine of the House of Saint Catherine features a set of buildings built around Saint Catherine’s old family house, including a beautiful arcade courtyard.

On-site, there’s also the Kitchen Oratory, the Oratory of the Bedroom, and the Church of the Crucifix. In the shrine, you can also see several paintings depicting the saint.

stonework facade of the basilica with a church tower
The exterior of the Basilica di San Francesco

Lastly, Basilica di San Francesco houses fragments of frescoes that used to cover two of Siena’s city gates, Porta Romana and Porta Pispini.

Furthermore, the church has some absolutely gorgeous stained glass windows!

Have one last dinner in Siena.

hand cut pappardelle with boar meat ragu meat sauce
Handmade pappardelle with boat, anyone?

Wrap up your second day in Siena with one more delicious dinner. Osteria Permalico is another charming restaurant worth checking out. 

Try some traditional pasta like the pappardelle with wild boar meat or buttera di cinta Senese (steak from a domestic pig from Siena).

Vegetarians, don’t worry, there’s options available for you too!

Where to Stay in Siena

The Siena cathedral as seen from above on one of the towers, great view of the belltower on a sunny day

LUXURY: Hotel Certosa di Maggiano

What could be more incredible than staying out in the Tuscan countryside? Staying in this former monastery converted into a luxury hotel, of course!

Its courtyard has been turned into a gorgeous terrace overlooking a beautiful pool, and every room in the place is dripping with history. The on-site restaurant is delicious, and yet you’re just over a mile from Siena’s Piazza del Campo.

MID-RANGE: Palazzetto Rosso Art Hotel

In a historic palazzo, this funky art hotel has been given a modern face-lift while enjoying some of the best Siena Old Town views — some rooms even have a bathtub that faces famous church domes!

The room style is geometrical and modern meets rustic (think elements like exposed brick and wooden beams). It’s eclectic, delightful, and full of personality!

BUDGET: La Villa

This converted 19th century villa hosts several charming rooms in a B&B style setup, a 10-minute walk from Piazza del Campo. 

There’s an on-site garden to relax in, where breakfast (additional charge) is served during the warmer months.

2 Days in Pisa: Itinerary to Explore this Beloved Tuscan City

The center of Pisa with some beautiful buildings on the waterfront

Pisa may be best known for its iconic Leaning Tower of Pisa, but there’s more to the Tuscan city than its famous crooked tower. 

Home to lovely medieval architecture, the world’s first university botanical garden, great museums, and amazing restaurants, Pisa is a perfect Tuscan city to explore on a weekend trip.

⌛ Planning your Pisa trip in a hurry? Here are my quick picks.

🏝️ Best Pisa Tours & Experiences
1. Leaning Tower & Cathedral Complex Tickets (#1 attraction in Pisa!)
2. Chianti Half-Day Wine Tour (top-rated wine tour)
3. Pisa Food Tour (tastings from 5 eateries on a lunch tour)

🛏️ Best Pisa Hotels
1. Grand Hotel Duomo (best Leaning Tower views!)
2. The Rif (art hotel in a renovated 1900s villa)
3. Palazzo Feroci (luxury converted palazzo with designer interiors)

✈️ Flying into Pisa? Book your airport taxi in advance with Welcome Pickups for a stress-free arrival.

🚘 Planning to travel around Tuscany independently? Look into car rentals in Pisa.

While living in Rome, I traveled to Pisa on one of my many trips across Italy, and I absolutely recommend spending a couple of days in the beautiful city. 

In addition to admiring the peculiar leaning tower, you can enjoy strolling along Borgo Stretto or the Arno River and sample delicious Tuscan food at charming local restaurants.

On the bank of the Arno River, the striped facade of the marble-faced Gothic church Santa Maria della Spina in Pisa
The lovely Santa Maria della Spina on the Arno

This 2 days in Pisa itinerary includes all the highlights in Pisa, from the complex with the Cathedral and Tower to some of the city’s the top museums. 

Even better, you can decide whether you join activities like wine and food tours!

You can easily adapt this Pisa itinerary to your needs by swapping things around to fit your schedule.

Where to Stay in Pisa

The Field of Miracles (also known as Campo dei Miracoli in Italian) as seen when photographed from the Grand Hotel Duomo
Want this view? Stay at the Grand Hotel Duomo!

BEST VIEW | For the most epic views over Pisa’s most famous attractions, Grand Hotel Duomo is all about a central location and views, including a rooftop terrace. With a rather affordable price tag, especially in the off-season, this is a great mid-range option in Pisa.

ARTSY BOUTIQUE | This trendy hotel has excellent amenities just a five-minute walk from Pisa’s Piazza dei Miracoli, making it central and incredible. Set in a renovated villa from the early 1900s, The Rif is dripping with artwork, including temporary exhibitions in the hotel! Plus, some rooms even have a spa bathtub.

DESIGNER LUXURY | In an old palazzo building in the center of Pisa, Palazzo Feroci is a fantastic choice for opulence and elegance, with interior design straight off of a Pinterest board. Rooms balance antique details like crown molding, intricate fireplaces, and exposed beams with avant-garde furnishings for a one-of-a-kind experience that isn’t cheap but is impossible to forget.

Day 1 of Your Pisa Itinerary 

Visit the monuments in the Square of Miracles.

The structure of the Duomo cathedral of pisa and the famous leaning tower of pisa, with lots of tourists around, on a clear sky day
The famous Leaning Tower and its neighboring Pisa Cathedral

As we’ve mentioned, Pisa is practically synonymous with its iconic Leaning Tower, but what you may not know is that the tower is just one piece of the complex of landmarks located in the same square. 

The square is officially called Piazza del Duomo but is commonly known as Piazza dei Miracoli, which means Square of Miracles.

The whole complex, including the Leaning Tower of Pisa and the Duomo, is called Opera della Primaziale Pisana.

Aside from the two major landmarks, it also includes the Baptistery, the Camposanto Cemetery, the Sinopie Museum, and the Opera del Duomo Museum.

The Baptistry of St. John, Pisa, a round building with white marble and a red tile roof, with lots of tourists around
The famous Baptistry of St. John, Pisa

You can easily spend an entire morning in the area, walking around the impressive monuments and visiting the ones you are most interested in.

Visiting all the monuments and museums of the complex takes at least half a day, so be sure to plan accordingly.

You can get a combined skip-the-line ticket that includes access to all the monuments, including the Tower, for 27€.

Buy your ticket online here to save time

If you just want to visit the Duomo, you might be able to get a free entrance ticket at the on-site office, but be aware that these are limited so you might not get in (go very early if you try this)!

Take in the sights of the Opera della Primaziale Pisana.

Famous Pisa cathedral with an interior view of the ceiling mosaics and frescoes, with religious iconography.
The interior of the Pisa Cathedral

The two must-see monuments are the Duomo and, of course, the Tower. 

The Duomo, or Pisa Cathedral, was built in the 11th century and is better known for its black and white marble façade and Islamic elements.

A devastating fire damaged the cathedral in 1595, so many elements were replaced in the early 17th century. 

The church houses several impressive artworks, from paintings and frescoes to the elaborate pulpit by Giovanni Pisano.

The other monument you should absolutely visit if you can is the Leaning Tower of Pisa, the symbol of the city. 

Lots of tourists around and at the top of the leaning tower of pisa, which tilts to the right side of the frame, on a sunny summer day.
The Leaning Tower of Pisa, the city’s icon

I mean, if you went to Pisa and didn’t take a cheesy picture of the tower, did you even go?

The iconic bell tower dates to the 12th century. Before construction could even be completed, the structure started leaning due to the soft ground.

The tilt worsened with time, reaching 5.5 degrees by 1990. Over the years, many interventions aimed to keep the tower from toppling but were unsuccessful.

After the tower’s closure in 1990, a new intervention from 1993 to 2001 successfully straightened the tower to a 4-degree tilt. 

To reach the top of the Leaning Tower, you must climb 296 steps, so get ready for a workout.

Unfortunately, this does mean that the visit isn’t suitable for people with certain health issues or disabilities, but the view of the outside is still worth the trip! 

While the Tower and the Duomo are absolute musts, you should also visit the other monuments. 

The Baptistery of St. John the Baptist is Italy’s largest baptistery and features sculptures and architectural elements by local artists like Nicola and Giovanni Pisano.

The interior is impressively vast, with a simple and nearly empty minimalist aesthetic, providing great acoustics.

The Camposanto Monumentale is a walled cemetery featuring elaborate arcades housing tombs and beautiful frescoes.

One of the landmarks of Pisa, the  Camposanto Cemetery, with famous dirt brought back from Calvary near Jerusalem. Walled cemetery on a clear, sunshiney day in the summer travel season.
The beautiful Camposanto Monumentale

The cemetery name, which translates to Sacred Field, is a reference to the soil on which it was built, brought to Pisa from Calvary, just outside Jerusalem, during the Third Crusade.  

Lastly, you can visit two museums housed in the Ospedale Nuovo di Santo Spirito, a former hospital dedicated to helping pilgrims, the poor, and abandoned children. 

The Opera del Duomo Museum displays decorative elements of the cathedral from its various stages, while the Sinopie Museum houses impressive preparatory drawings used by artists to paint the frescoes in the Camposanto.

Have a lunch break.

Narrow central area with a cozy side street in Pisa, with trattorias and restaurants
So many cozy trattorias and osterias in the center of Pisa!

After visiting some or all the monuments in the Square of Miracles, depending on your pace, it’s time for a lunch break.

If you want to stay in the area to complete your visit in the afternoon, have a quick lunch with tasty pizza or sandwiches at Po’stò Cafè Pisa or try the delicious pasta dishes at Il Peperoncino.

Alternatively, if you’re ready for a change of scenery, walk towards Pisa’s historical center, roughly 10 minutes away, and have lunch in a rustic Tuscan restaurant at Osteria del Tumi.

 A black chalkboard menu with a list of dishes in front of a restaurant in pisa city center.

Enjoy delicious pasta or try one of the traditional meat-based Tuscan specialties if you’re in the mood for something hearty.

Their wild boar ragu with polenta is famous!

Explore Pisa’s historical center.

Some colored buildings on a narrow small street in Pisa, with storefronts, arches, and residential buildings up top.
The Borgo Stretto area of Pisa

In the afternoon, you can either go back to visit any monuments or museums you skipped in the Square of Miracles or head directly to Pisa’s historical center.

One of the most charming areas, located right in the heart of the historical center, is Borgo Stretto.

Borgo Stretto translates to “Narrow Village” and is a long and narrow commercial street starting in Piazza Garibaldi and ending at Galileo’s statue

A bronze-made statue featuring Giuseppe Garibaldi in Garibaldi Square in Pisa's center
The Giuseppe Garibaldi statue from in 1892, made by Ettore Ferrari

The colorful buildings on both sides of the street have arcades, providing a pleasant strolling experience any time of the year.

Simply walk down the street and check out the historical buildings and shops, or maybe stop for a coffee at a bar.

Another place worth checking out is the vast Renaissance-era square Piazza dei Cavalieri

a clocktower with an arch, other brick buildings with italian flag, people walking around, orange and pastel colored facades in a piazza in pisa
Buildings in Piazza dei Cavalieri (Knights Square)

It’s surrounded by gorgeous buildings like the Palazzo del Consiglio dei Dodici and the imposing Palazzo della Carovana housing Pisa’s faculty of science.

Another key landmark is the Palazzo dell’Orologio, a medieval building incorporating the ancient Torre della Muda.

This famous tower is notable for being mentioned in Dante’s Divine Comedy. 

Torre della Muda with its arches and clock at the very top

The statue in front of the university building represents Cosimo I de Medici, the first Grand Duke of Tuscany.

Take some time here to wander around the cobweb of narrow streets around Pisa’s historical center; there’s some remarkable beautiful medieval architecture to admire!

Stop by the charming Piazza Carrara, stroll along the Arno River (yup, the same river that runs through Florence), and check out Casa Ammannati, the birthplace of Galileo Galilei.

Visit one of Pisa’s excellent museums.

Blue building of Palazzo Blu with other buildings along the Arno waterfront in Pisa, with reflection on a sunny day
Set along the Arno, Palazzo Blu is the (shocker!) blue building that hosts an art museum

If you have any time left in the afternoon, you can visit one of the many museums in Pisa.

Two museums worth checking out are Palazzo Blu and Museo delle Navi Antiche di Pisa.

If you are passionate about art, Palazzo Blu houses an impressive collection of paintings related to the city of Pisa, either made by local artists or representing the city. 

The artworks cover a span of seven centuries, from the 14th to the 20th centuries.

In addition to the permanent collection, you may check out temporary exhibitions, all for an entry ticket of just 3€ — one of the best deals in Italy!

Plan your visit ahead of time, though! The museum is closed on Monday.

Interior of history museum / Image Credit: SailkoOwn work, CC BY 3.0, Wikimedia Commons

On the other hand, Museo delle Navi Antiche di Pisa is a modern history museum dedicated to telling the story of Pisa through the centuries, starting from its settlement and passing through the Etruscan and Roman phases.

The museum also houses a collection of ships and related artifacts, including remains of ancient Roman ships.

The entry ticket for the museum is 10€, and you can also purchase it online.

You can visit by yourself from Friday to Saturday or join a guided tour on request from Tuesday to Thursday.

Have dinner and stroll along the Arno.

Night view of the lit up colorful houses along the Arno river waterfront in Pisa's city center
View at night along the Arno

End your day with dinner in a traditional Tuscan restaurant followed by a pleasant stroll along the Arno River. 

For dinner, you ca try a tasty pasta dish or enjoy traditional Tuscan meat dishes at either Ristorante alle Bandierine or Il Ristoro della Pe’ (with some delicious local Italian wine, of course). 

After dinner, head to Lungarno Antonio Pacinotti and walk along the river to enjoy the beautiful view of the city at night.   

Day 2 of Your Pisa Itinerary

Go on a half-day wine-tasting or food tour.

A man and a woman holding up two scoops of gelato with a backdrop of the Arno River in Pisa Italy

A great way to spend half a day in any Tuscan city is to join a wine tour in one of the charming hill towns of Tuscany.

Most cities in the region provide such activities, and Pisa is no exception!

These activities allow you to escape the buzzing city and admire the region’s rolling hills and wineries, all while sipping on a good glass of Tuscan wine

Be warned that some of these activities may not be available during winter months.

If you visit from November to February, you can always replace these with more museum visits.

Option One: Half-day Chianti Wine Tasting

a glass of wine with an out of focus landscape behind it

This 4-hour wine-tasting tour is a great activity if you are short on time but want to get a taste of the wonderful Chianti region.

You’ll get a guided tour of a local winery just outside Pisa to learn about wine and olive oil making and sample red and white wine.

The small-group tour is available for a minimum of two people and includes transportation, a tour guide, a winery tour, and wine tasting.

It doesn’t include lunch, so bring snacks!

Option Two: Winery Tour in the Tuscan Countryside

view of wine regions of florence's surrounding area of tuscany

This food and wine tour in the Tuscan countryside lasts around five hours and includes a visit to a wine estate with lessons on wine and olive production techniques.

You’ll sample a selection of local wines paired with delicious Tuscan farm-to-table products.

This tour is also available for at least two people and includes everything from the guide and transportation to food and wine.

You can even request hotel pick-up and drop-off at select hotels. 

If you choose to check out this activity, book well ahead of time, as it can sell out for weeks in advance.

Option Three: Pisa Food Tour

hand holding a gelato in a gelateria

If you prefer staying in Pisa rather than exploring the countryside, such as if you’ve already explored a Tuscany itinerary, you can also join this food tour in the heart of Pisa.

You’ll stop by five local eateries to experience the authentic flavors of Pisan cuisine, from local cheese and cured meats to traditional soups and stews.

You’ll also get to try the famous cecina (chickpea flatbread), and of course, finish the tour with some delicious gelato.

Typical Italian chickpea pancake, a rustic cake, served with focaccia

This food tour lasts roughly 3.5 hours, starting in the late morning, so it’s the perfect lunchtime activity. Like many activities, this tour also requires a minimum of two participants. 

If you decide to do this instead of the wine tour, you can spend the morning exploring the city or visiting a museum that you didn’t get to yesterday.

If you opt for the wine tour instead, you may want to have lunch once you’re back in Pisa.

I Porci Comodi and L’Ostellino are great spots for quick and delicious sandwiches.

Explore more areas of Pisa.

One of the buildings of Piazza Vittorio Emanuele square, the lovely beige colored St Anthony Abbey, a Catholic church in Pisa.
St. Anthony Abbey on Piazza Vittorio Emanuele

In the afternoon, you can cross the Arno and explore the sights on the southern riverbank.

Cross Ponte di Mezzo for a lovely view of the river flanked by the colorful buildings, then stroll along Corso Italia, the main shopping street lined with all kinds of shops.

Near Piazza Vittorio Emanuele II, you’ll find a building covered in a massive mural by Keith Harring, Tuttomondo.

From here, walk back toward the river to check out the charming Chiesa di Santa Maria della Spina, a small 13th-century church with a beautiful Gothic façade.

Cross the river on Ponte Solferino and find your way to the Botanical Garden and Museum.

The Arno River with the Ponte Solferino bridge spanning across it, framing colorful houses of the Arno Waterfront.
The lovely Ponte Solferino bridge

The botanical garden belongs to the University of Pisa and is the world’s first university botanical garden, founded back in 1543.

The garden was originally on the riverbank but was moved to its current location in 1591.

Along with the stunning botanical garden housing plants from all continents, you can visit a museum dedicated to the teaching of botany.

You can book your tickets online to save time when you get there.

Rest and have one last dinner in Pisa

The 16th century style of palace in the Gothic revival architecture, known as Palazzo Vecchio de' Medici, along the Arno River
The lovely riverside Palazzo Vecchio de’ Medici

You can spend the rest of the afternoon and early evening resting in your hotel or wandering around the city before heading to dinner.

If you decide to explore more, you can check out Chiesa di Santa Caterina d’Alessandria, the ruins of the Baths of Nero, Porta a Lucca, and the Medici Palace.

Finally, have one last delicious Tuscan dinner at Ristorante Cantina Vasari or Ristorante Allabona.

After dinner, you can enjoy a relaxed stroll around Borgo Stretto to enjoy the peaceful atmosphere without the day crowds.

Medieval Monteriggioni: 11 Marvelous Things to Do in this Lovely Walled Town

monteriggioni streets in the city center with cobblestone and old brick buildings

Wandering the medieval streets of Monteriggioni, it’s easy to feel like you’ve stepped into bygone era, Outlander-style.

Located along the Via Francigena route, Monteriggioni simply couldn’t get any cuter.

This entirely-walled-in small village is part of the Tuscan province Siena, and definitely vies for the prize of being one of Tuscany’s most scenic towns.

backroads of tuscany

And who can blame it? Monteriggioni exudes an air of timeless charm that’s hard to resist and easy to lose yourself in.

We could blab on and on about its narrow alleys, medieval architecture, and panoramic views of the rolling hills of Tuscany.

But really, it’s the ineffable things: the peaceful vibe that can only be found in an ancient, historic small town that makes it so compelling. 

Read on to figure out why this town is a must-see on Tuscany road trips and day trips from Florence!

Note that it can be difficult to get here with public transit — so renting a car is the best way to see Monteriggioni.

This is a great day trip to make while you’re staying in one of the Tuscany pool villas in the area, too!

A Brief History of Monteriggioni

a town in monteriggioni with blue shutters, lots of plant life, stonework

Monteriggioni’s history dates back to the early 13th century when the town was first built. It was intended as a strategic outpost for the former Republic of Siena (so-called before the Unification of Italy).

Strategically atop a hill, its convenient location was home to impressive stone walls that enclosed the city — and 14 towers used for defensive surveillance — were witness to countless battles between the powerful city-states of Siena and Florence, which was home to the tour-de-force that was the Florentine empire. 

Today, Monteriggioni stands as a testament to medieval engineering and offers visitors a rare glimpse into Italy’s rich past pre-unification.

Things to Do in Monteriggioni

Admire the Castello Monteriggioni.

old castle preserved well with arch, towers, walls, gate

The Castello Monteriggioni is the focal point of the town, a striking fortress that dominates the skyline with its imposing walls and towers. 

Bearing witness to the wars of the 13th century, this well-preserved castle once had a major role as strategic outpost. 

Today, the Castello Monteriggioni is both a historic site as well as providing an awe-inspiring photo backdrop!

Wander amongst its incredible walls and towers.

the walled-in city of monteriggioni in tuscany

To fully grasp the scale of Monteriggioni’s formidable defenses, be sure to walk along the ancient city walls that still encircle the town.

It’s even more impressive when you think about how old it is — and how perfectly preserved the high walls remain today.

The nearly 600-meter-long fortification provides a fantastic opportunity to admire not only the expert engineering, but also the surrounding countryside and the town’s towers up close. 

For a small fee, you can also climb one of the towers and enjoy a bird’s-eye view of the town and the picturesque Tuscan landscape beyond.

Explore the Arme Museum.

The Arme Museum (written as the Monteriggioni in Arme in Italian) is a fascinating local attraction that’s great for history geeks and military buffs.

This small but mighty museum shows the town’s military history through an extensive collection of artifacts: in particular, medieval weapons and armor. 

Located within the ancient city walls of Monteriggioni, this small museum offers an immersive experience into what Monteriggioni was like before its current iteration.

Walk through Porta Romana and Porta Fiorentina.

Fortified walls of the small town of Monteriggioni, with ivy and trees

One of the main gates of Monteriggioni, Porta Romana and Porta Fiorentina are key landmarks you can’t miss while visiting Monteriggioni.

The fact that they still exist is a testament to both the town’s strategic importance and impressive fortifications and the well-engineered nature of them, as they still exist beautifully today. 

These well-preserved gate, adorned with the emblem of the republic of Siena, provides a fitting entrance to the enchanting walled town. 

As you pass through Porta Romana and Porta Fiorentina, you’ll immediately be transported back to a time when Monteriggioni served as a critical outpost in the ongoing struggle between Siena and Florence.

Take a wander through the Old Town.

Narrow town streets in Monteriggioni town in Tuscany

One of the best ways to appreciate Monteriggioni’s unique charm is to simply wander through its narrow streets, allowing yourself to be enveloped by the town’s enchanting atmosphere. 

The rustic stone houses adorned with colorful flower pots and the sound of laughter emanating from local trattorias make this town feel simultaneously ancient and utterly alive.

Learn more history at the Museo delle Armature. 

There’s even more war history here at the the Museo delle Armature (Italian for the Armor Museum). 

This little museum showcases a varied collection of armor, weapons, and other historical artifacts that show the extensive craftsmanship of this period.

Kill some time in Piazza Roma.

Main square in Monteriggioni medieval fortified on the route of the via francigena, in Tuscany

Piazza Roma is the heart of modern Monteriggioni. 

While much of the city is stepped in the past, Piazza Roma is very much in the present: a picturesque square surrounded by stone buildings and people going about their day. 

There are a few key buildings on the Piazza, including the magnificent Church of Santa Maria Assunta. 

This is a great place to kick your feet up after wandering the walls — grab a cappuccino and soak in the enchanting atmosphere of this medieval gem. 

Wander through the Giardino Pubblico.

Monteriggioni’s Public Garden, also known as the Giardino Pubblico, is a peaceful oasis within the town’s ancient walls.

With its green, quiet ambiance and ample shaded benches, this charming garden offers many places to sit and escape the buzz of the town. 

Enjoy a leisurely picnic here, or simply bask in the serenity of this garden amidst an enchanting medieval town.

Visit the Church of Santa Maria Assunta.

Santa Maria Assunta Church in Monteriggioni

Make sure to visit the central Piazza Roma, where you’ll find the Church of Santa Maria Assunta, a lovely example of Romanesque architecture. 

This 13th century church is known for its rose window, stripped-down façade, and stone gate. 

Small with just one nave, it’s still an incredibly remarkable church, with exquisite frescoes featuring biblical scenes like that of the Madonna and her child.

Visit in time the Monteriggioni di Torri Si Corona festival.

For a truly unforgettable experience, visit the medieval town during its famous Monteriggioni di Torri Si Corona in July.

The entire town transforms into a medieval wonderland complete with knights, jesters, and all sorts of characters from the Middle Ages.

Explore Monteriggioni’s food scene.

Tables of an Italian restaurant in the street of Monteriggioni, Italy

No visit to Tuscany would be complete without indulging in the region’s renowned gastronomy, and Monteriggioni offers plenty of opportunities to do just that! 

Cozy trattorias and rustic osterias serve up delicious traditional Tuscan fare such as ribollita, pappa al pomodoro, and pici. 

Better yet, pair your meal with a glass (or two) of the local Chianti wine, and you’ll have a dining experience that is nothing short of divine.

Where to Stay in Monteriggioni

Monteriggioni boasts a selection of charming accommodations that perfectly complement the town’s timeless allure. 

From rustic agriturismos to elegant boutique hotels, you’ll find a range of options to suit every taste and budget. 

One of our favorites is the Castel Pietraio, a beautifully restored medieval castle offering luxurious rooms and an idyllic setting amidst the rolling Tuscan hills.

15 Most Picturesque Towns in Tuscany to Visit

the hilltop town of montalcino in tuscany cascading down the hillside with stone structures and green trees

While the big, famous cities like Florence, Siena, and Pisa are mandatory stops for any visitor traveling to Tuscany, the Central Italian region is also home to countless delightful little towns.

Although they fly under the radar for most travelers, a closer look reveals that these charming little locales are just as worthy of attention.

The hills and valleys of the Tuscan countryside are dotted with medieval hilltop towns known for their gorgeous and well-preserved architecture, beautiful churches, and lovely museums. 

the famous road in tuscany with the cypress trees in autumn

Of course, since it’s Tuscany, you’ll also find exquisite restaurants serving traditional food and local wines.

During the decade and a half when I lived in Rome, I frequently traveled to Tuscany, most of the time on road trips through Tuscan towns.

No matter how many times I went, the beautiful region kept calling me back again and again to visit its beautiful art cities and charming towns. 

It’s the perfect place to rent a car, forget your plans, and just go!

In this guide, I’ve included a selection of the most picturesque towns across Italy’s scenic region in case you want to plan your Tuscany trip in more detail.

Many of these towns are home or close to some of these Tuscany villas with private pools — so they can make great side trips to explore from your villa home base!

The Most Beautiful Towns in Tuscany

San Gimignano

view of the city of san Gimignano with its medieval stone towers protruding from the rest of the skyline of the hillside town

This iconic hilltop Tuscan town is known for its many towers. In fact, that reputation extends so far that some people have called it “the Medieval Manhattan”. 

According to local history, back in medieval times, rival local families started building towers to show off their power and wealth.

Regardless of how they came to be, out of the 72 towers originally built in San Gimignano, only 14 are still standing.

Needless to say, when you see towers stretching to the sky, only one thing comes to mind: climbing to the top!

Lucky for you, you can enjoy the panoramic views from the 54 meters height of Torre Grossa or from Torre Salvucci Maggiore, the highest of the so-called Twin Towers of San Gimignano.

Unfortunately, you cannot climb the rest of the towers.

Other must-see sights in town include: the gorgeous medieval square Piazza della Cisterna; the town’s cathedral, Duomo Collegiata di Santa Maria Assunta, with its beautiful Renaissance frescoes; and Rocca di Montestaffoli, a former fortress surrounded by a beautiful park and offering panoramic views.

San Gimignano is in the province of Siena, roughly an hour northwest of the city. You can also get there from Florence in about an hour of driving or 1.5 hours by public transport.

Volterra

the beautiful town of volterra in italy

Just over half an hour’s drive from San Gimignano, you can reach Volterra, a lovely medieval town known for its ancient Etruscan heritage. 

Just outside the town center, you can find the ruins of the Etruscan acropolis, and nearby you can visit the Etruscan Museum “Mario Guarnacci.”

Volterra is also home to Roman ruins, the most prominent being the Roman Theater.

For a free panoramic view of the theater ruins, head to the viewpoint on Via Lungo le Mura del Mandorlo.

The heart of Volterra is its medieval center, enclosed within walls dating back to the 13th century.

The town originally had six entrance gates, built between the 13th and the 16th centuries. 

While you’re in town, explore the charming Piazza dei Priori with the imposing town hall Palazzo dei Priori, check out the ancient gate Porta all’Arco, and visit the 12th-century Cathedral of Santa Maria Assunta.

Certaldo 

a beautiful street in certaldo, tuscany, with buildings with greenery alongside the face of the building

Certaldo is a small town in Valdelsa, the valley along the Elsa River, southwest of Florence. 

Somewhat notably, Certaldo is divided into two parts, the modern lower town, and the old upper town, connected by a mountain cable car.

Although cars can reach the upper town, only residents are allowed access with a vehicle.

The old town of Certaldo is the main attraction, with its narrow medieval streets and charming red brick houses.

The main landmarks in Certaldo Alto are the Palazzo Pretorio (the former residence of the Florentine governors) and Chiesa dei Santi Jacopo e Filippo.

Certaldo is the hometown of Giovanni Boccaccio, a Renaissance Italian writer most famous for The Decameron.

One of the main streets in Certaldo Alto is dedicated to the writer, and his former house is now a museum.  

Monteriggioni

the walled-in city of monteriggioni in tuscany

Halfway between Siena and San Gimignano, you’ll find the medieval walled town of Monteriggioni, with its watchtowers and ancient gates overlooking the beautiful Chianti region surrounding the town. 

The Republic of Siena built the town in the early 13th century as a defensive fortification in the war against Florence.

You can explore most of Monteriggioni in just a few hours. The best thing to do in town is to walk along the fortified walls and enjoy the gorgeous views over the Tuscan hills. 

Most of the activity in town happens around the main square, Piazza Roma, so be sure to stop by.

After wandering around the little streets and gardens within the walled town, enjoy a coffee or lunch in Piazza Roma.

Have a delicious Tuscan meal at Ristorante Le torri Monteriggioni or Osteria Antico Travaglio.

Suvereto

Medieval village of Suvereto in Tuscany not far from the coastline of Livorno, quiet streets and old buildings

Not far from Tuscany’s gorgeous coastline, Suvereto is a small town in the province of Livorno. 

Towering over the medieval town, the Rocca Aldobrandesca is a former castle built by the Aldobrandeschi noble family in the 12th century.

The castle ruins offer beautiful panoramic views of the Tuscan countryside!

Suvereto is a quaint town, providing the perfect escape from the crowds that fill more popular places.

If you’re feeling overwhelmed by the big cities, take a few hours to enjoy strolling around medieval alleys in a bit of peace and quiet instead. 

Restaurants and wine bars are plentiful in Suvereto, so stop for lunch and enjoy traditional Tuscan dishes at Locanda Delle Stelle or Sughereto Vino e Cibo.

For a tasting of the (marvelous) local wine, head over to Enoteca Le Carceri.

If you’re up for visiting a quirky, one-of-a-kind museum, check out Museo Artistico della Bambola, a small museum displaying dolls of all kinds. 

For those lucky enough to visit in summer, catch a movie under the stars at the open-air movie theater Cinema Sotto le Stelle.

Montepulciano

the hillside town of montepulciano, also a famous wine destination, with greenery around the hilltop town

Perched at the top of a limestone hill and surrounded by beautiful vineyards, Montepulciano is probably best known for the grape variety and red wine that share its name. 

The top thing to do in Montepulciano is to stroll around its picturesque historic center and explore the lovely streets and charming squares.

Piazza Grande is the town’s main square, surrounded by historical buildings like Palazzo del Capitano del Popolo, Palazzo Nobili-Tarugi, and the town hall with its iconic tower offering sweeping views of the Tuscan hills.

Hidden away in a corner of the square, you can find an ancient well, Pozzo dei Grifi e dei Leoni.

Another must-see landmark in town is the Medici fortress, located at the highest point in town.

The defensive fortress dates to the 13th century and boasts stunning views and a gorgeous garden. 

Just outside the town center, visit the impressive 16th-century Sanctuary of the Madonna di San Biagio.

This is not the easiest place to get to without a rental car, so I suggest planning it only if you have one.

Pienza

The charming hillside town of Pienza with stone walls, stone architecture, church steeples, cypress trees

Less than half an hour east of Montalcino, Pienza is another delightful town in the Val d’Orcia.

The valley is one of the most beautiful in Tuscany, made famous by the iconic hilly landscape and the many vineyards that sprawl over its slopes.

In 1996, the historic center of Pienza was made a UNESCO World Heritage Site.

Historically, the town was named Corsignano, and it first appeared in the historical record in documents from around the 9th century. 

In the early 15th century, Aeneas Silvius Piccolomini was born in Corsignano and went on to become Pope Pius II in 1458.

Pope Pius II decided to rebuild Corsignano as an ideal Renaissance town and named it Pienza, which translates to “the City of Pius.”

One of the first buildings he ordered in the town center was the summer residence Palazzo Piccolomini, now a museum.

Other buildings part of the Renaissance reconstruction are the Pienza Cathedral, Palazzo Borgia, which now houses the Diocesan Museum, and the city hall.

The historic town of Pienza has many viewpoints overlooking the fascinating Val d’Orcia.

San Quirico d’Orcia

The church of San Francesco in Liberty square in the town of San Quirico d'Orcia

Halfway between Montalcino and Pienza, you can find the small town of San Quirico d’Orcia.

It’s best known as a stop along the Via Francigena, the famous pilgrimage route that runs from Canterbury in England all the way to Rome.

The picturesque little town makes for a great stop on a road trip around the beautiful Val d’Orcia.

The landscape surrounding the town boasts rolling hills and beautiful cypresses. 

In the small historical center, you can visit the lovely Collegiate Church of San Quirico and walk around the delightful, landscaped garden of Horti Leonini.

If you want to stop for lunch in San Quirico d’Orcia, try a light meal at La Bottega Di Portanuova or a charcuterie board with a glass of local wine at Vald’O la Vineria Letteraria.

A few minutes south of San Quirico d’Orcia, you can visit the hilltop fortress Rocca di Tentennano for a spectacular panoramic view of the stunning landscape.

Montalcino

the hilltop town of montalcino in tuscany cascading down the hillside with stone structures and green trees

Less than an hour south of Siena, the hilltop town of Montalcino is your typical Tuscan medieval town.

With a charming old town and beautiful views over the surrounding Val d’Orcia, Montalcino is the perfect little destination in the Tuscan countryside.

Visit the Fortress of Montalcino to take in the beautiful view of the town’s medieval center and discover the lovely Cathedral of the Holy Savior. 

A short walk or drive outside the town center, enjoy more striking views from the viewpoints Belvedere di Montalcino or Panorama della città e della Valle.  

Like many towns in the area, Montalcino is renowned for its wine production, which is a local specialty. 

Brunello di Montalcino is the most famous wine produced in the area and among the most prestigious Tuscan wines. Try a glass with a tasty pasta dish at Il Moro or Re di Macchia.

Pitigliano

A view of ancient Italian town Pitigliano from autumn park in Tuscany, Italy

Located in the province of Grosseto, near the border with the Lazio region, Pitigliano is a small but charming town built on top of a tuff cliff. 

From a distance, the houses seem to emerge from the tuff rock to gather around the imposing bell tower of the Pitigliano Cathedral.

The town is known for its large Jewish community, and the presence of a synagogue as well as an ancient ghetto known as the “Little Jerusalem,” which is now home to a museum.

Simply meandering through the narrow alleys of Pitigliano’s old town is the best way to spend your time in town. 

There’s a great view from the iconic Fontana delle Sette Cannelle, and you can visit the small but lovely Museum of Palazzo Orsini. 

For a beautiful view of the town from a distance, drive or walk along Via San Michele, toward the cemetery.

Cortona

the town center of cortona with a famous clocktower and square

Not far from Arezzo, close to the border between Tuscany and Umbria, you’ll find another picturesque hilltop town, Cortona. 

Like many old towns in Tuscany, Cortona has a rich Etruscan heritage that you can learn about in the Etruscan Academy Museum.

For sweeping views over the Tuscan countryside, head to the Fortress of Girifalco, an ancient fortress renovated by the Medici family in the 16th century. Every year, the structure houses an international photography festival called Cortona on the Move.

Other landmarks of note include the Cortona Cathedral, the beautiful medieval square Piazza della Repubblica, and the opulent Basilica of Saint Margaret of Cortona. 

For a fantastic Tuscan meal, check out La Bucaccia – Da Romano or the rustic Osteria del Teatro.

Anghiari

the town of anghiari with charming medieval streets and winding roads

The small town of Anghiari in the province of Arezzo is best known for the 1440 Battle of Anghiari between the forces of Milan and Florence. 

This battle ended with the victory of the Florentines and led to their subsequent domination over central Italy. You can learn more about the historic battle at the Museo della Battaglia di Anghiari.

For such a small medieval town, Anghiari has quite a few attractions, including the art collection at Museo di Palazzo Taglieschi.

There are also the frescoes inside the Church of Sant’Agostino, and even a reproduction of the Last Supper inside the Church of Santa Maria delle Grazie.

After exploring the delightful medieval town, head outside the walls to wander along the walking paths and enjoy the view of the surrounding valley.

Barga

View of Barga, a colorful medieval town that was designated one of the "most beautiful villages in Italy"

Less than an hour north of Lucca, Barga is a medieval town in the Media Valle, a valley along the Serchio river enclosed between the Apuan Alps and the Apennines.

Barga is known as Italy’s most Scottish town. The unique name is due to the many locals who emigrated to Scotland in the 20th century and returned to their hometown many decades later. 

One of the most curious things you’ll find in Barga is a typical British red telephone box, which is now used as a little public BookCrossing library!

Chief among the main sights in Barga, you can’t miss the beautiful Collegiate Church of San Cristoforo or the ancient aqueduct. 

The town is also home to an unusually large numberof art galleries where you can check out the works of talented local artists.

Saturnia

the hot springs in saturnia with lots of people enjoying the cascading hot psrings

The spa town of Saturnia is among Italy’s most iconic spots, famed for its stunning thermal waterfalls, Cascate del Mulino.

The town of Saturnia counts fewer than 300 full-time inhabitants but draws thousands of visitors who come to bathe in the picturesque thermal pools.

Thanks to its unique setting, Saturnia has been inhabited since ancient times, even before the ancient Etruscans. 

Formerly known as Aurinia, the town got its current name from the Roman god Saturn.

According to legend, the great god grew tired of witnessing constant wars among humans, so he struck the earth with a thunderbolt that created these magical springs, which were supposed to bring peace among mankind.

The Roman ruins in Saturnia are a testament to ancient times, but there is little else to visit in town.

Check out the Church of Santa Maria Maddalena and Rocca Di Saturnia, then head to the Terme di Saturnia and relax in the beautiful springs.  

Castiglione della Pescaia

the gorgeous seaside landscape of castiglione della pescaia, one of the most beautiful towns in tuscany

Castiglione della Pescaia is a small seaside town in the province of Grosseto, in southwest Tuscany. The modern town developed around the hilltop Castello di Castiglione della Pescaia, which is now privately owned.

This unassuming town was chosen as a residence by many celebrities and personalities, from actors and film directors to writers and political figures, including Roger Moore, Sophia Loren, and even the former King of Spain, Juan Carlos I.

This is probably why the town is home to Italy’s second-most expensive street for house prices, with the first being in Montalcino.

Check out the beaches along Via Roma, explore the old town right below the castle, and enjoy delicious food at one of the many restaurants in town, like Ristorante Arturo or Clann. 

Just south of town, you can have a truly unique wildlife experience admiring the flamingo colony in the nature preserve Riserva Naturale Diaccia Botrona.

Tuscany Road Trip: The Perfect 5 Day Tuscany Itinerary

the beautiful road leading to the val d'orcia in tuscany italy, with cypress trees flanking a narrow, winding hillside town

Rolling hills with perfect rows of manicured vineyards, hilltop towns with medieval architecture, and some of the best food you’ll find in all of Italy: these are just three of the reasons to take a Tuscany road trip.

While you can go on day trips to Tuscany from Florence, the best way to explore the scenic Tuscan countryside is to rent a car and drive through it yourself!

A Tuscany road trip will take you through some of the most beautiful villages and medieval towns in Italy, with lovely historical centers, beautiful churches, and spectacular castles.

Cozy narrow street decorated with colorful flowers in the charming town of Pienza in Tuscany, a small and historic village.
The beautiful town of Pienza is a must on any Tuscany road trip!

Whatever season you visit Tuscany in, this picturesque region will reward you with spectacular views and unforgettable experiences.

To help you ensure you won’t miss any must-see sights, I put together an itinerary with some of the best spots to visit on this road trip through Tuscany.

In just 5 days in Tuscany, you’ll be driving through the region’s most beautiful cities and villages, tasting great local wines, and — perhaps most importantly — enjoying delicious food!

All you need to do is book your flights and rent your car, and you’re ready to fall in love with Italy’s most charming region — I’ve done all the legwork for you!

What to Know Before Planning your Tuscany Road Trip

The road leading to the La Foce gardens in the southern part of the Val d'Orcia, with cypress trees on both sides of the road
Driving in Tuscany brings you to beautiful places, like the road heading to La Foce Gardens in Val d’Orcia.

Before getting into this Tuscany road trip itinerary, it’s worth covering a few practical details you should be aware of.

Driving in Italy is not without its quirks, so here are the most important things to keep in mind before driving through Tuscany!

Hopefully, these tips will help you plan the Tuscan road trip of your dreams.

We also suggest reading this guide to renting a car in Tuscany before your trip, as it gives helpful driving tips for the region.

Best Time for a Tuscany Road Trip

Winding road to a village in Tuscany with mustard flowers lining the fields in the springtime.
Tuscany road trips are perfect for summer or fall — summer can be busy and hot!

Tuscany is beautiful any time of the year but the ideal time for a road trip is either late spring or autumn.

Although in summer the region is also beautiful, the months of July and August are also the busiest, so you’ll risk finding many places crowded and everything pricier.

Plus, everything is hot, hot, hot, and most of the joys of a trip in Tuscany is spending time outdoors.

Whether it’s sitting on patios that overlook vineyards sipping local Chianti or wandering through an ancient city street…. none of that is fun when the temperatures are so high you feel like you’re melting!

Spring is a great season to enjoy beautiful landscapes, with flowers blooming and the typical Tuscan hills covered in all shades of green.

The temperatures are also pleasant if you visit in late April and May, and as long as you prioritize the early part of June, June is still a good month to visit.

Colorful autumn vines with red, yellow, and orange leaves on the grapevines in the wineries of Tuscany
Autumn is a great time to do this Tuscany itinerary!

Since Tuscany is famous for its wines, autumn is also a great time to visit the countryside and enjoy wine tasting in Tuscany while admiring the hard work that goes into getting ready for the harvest season.

Best of all, the temperatures are still pleasant from mid-September to late October, and the crowds get smaller, so the season is perfect for a road trip!

If you’re wondering whether you could do a road trip in winter, the answer is yes.

However, it can get quite cold, the landscape is not nearly as pretty, and you’ll also find some restaurants and museums closed for the season.

On the bright side, you’ll find lower prices and no crowds — it may be worth it, but I don’t think it’s the best time of year.

Driving in Tuscany

A woman hanging out of the passenger window to take in the view from a Tuscan road
Driving in Tuscany is pretty easy if you know a few key things beforehand.

Driving through the Tuscan countryside doesn’t pose any particular issue.

Even as a foreigner, you should have no problem getting around — as long as you have an international driving permit (IDP).

You’ll mostly be driving along regional roads, but from time to time, you may take the highway, which has tolls.

You shouldn’t expect to pay much, but having some coins always with you can be handy.

Most tollbooths take credit or debit cards too, but sometimes you may not have this option, so don’t get caught off guard!

Even if you visit Tuscany in winter, which is not a popular season for road trips, you shouldn’t worry.

Temperatures rarely go below 0°C (32°F), and snowfall is uncommon, so there are no particular hazards when it comes to driving in Tuscany in winter.

Wine Tasting and Driving in Tuscany

Outdoor tasting of white wines with vineyards in the background
No road trip to Tuscany is complete without trying its wines — responsibly, of course!

No trip to Tuscany would be complete without some wine tasting, of course!

But if you’re road tripping in Tuscany, you need to be aware of both laws regarding alcohol consumption and driving and, of course, your safety (and the safety of others on the road with you!)

According to Italian law, you can drive with a maximum blood alcohol content (BAC) of 0.05% if you are over 21. Younger drivers are not allowed any alcohol if driving.

While the BAC depends on various factors, from your gender to your weight and whether you drink on a full or empty stomach, a good rule of thumb is to minimize your alcohol consumption as much as possible.

Here are some charts that help you calculate your BAC, so you can know how many glasses of wine you can safely consume before driving.

The bottom line is, while alcohol is always better avoided before driving, by law, you can have a glass or two of wine with your meal and drive, depending on a variety of factors.

If you’re traveling with a partner or group of friends, this is ideal as you can take turns for who can wine taste and who is the designated driver throughout the trip.

Where to Begin Your Tuscany Road Trip

View of the Duomo in Florence from the other side of the Arno River, with the Duomo visible and other towers, and hills in the background
Florence makes the most natural starting point for a Tuscan road trip.

The best place to start your road trip around Tuscany is the region’s capital and biggest city, Florence — plus, it’s just a marvelous city to visit as well, home to sites like the Statue of David and the Florence Duomo.

Be sure to dedicate at least one day in Florence before exploring Tuscany, unless you’ve been there before and feel like you’ve already covered the city!

The international airport Firenze-Peretola has flights to and from many European cities, making it a great place to start your road trip.

Furthermore, you’ll find plenty of high-speed trains going to Florence from all the other big cities in Italy.

A train ride from Milan only takes two hours, while Rome is just over one hour and a half away.

While you could base yourself in Florence and just do several day trips, a Tuscany road trip allows for far more freedom and way less back-and-forth trips.

How Many Days for a Tuscany Road Trip?

Interior of a car in Tuscany overlooking a winery with a white building and mountains in the background
You can take however much time you like, but I recommend 5 days in Tuscany (or more)!

You could easily spend two weeks driving around Tuscany, and you’ll still come across new, wonderful places — that’s the marvel of this region.

On the other hand, you could potentially cut this road trip significantly, and you could even condense this itinerary down to a three-day road trip to see some of the main sights.

However, anywhere between five and seven days for a Tuscany road trip is a good option.

This way, you don’t have to rush and you still get to see the most important places.

As written, this Tuscany itinerary takes five or six days, depending on whether you spend one or two nights in Siena — a city so marvelous it deserves a little extra time.

You can combine this itinerary with a two or three-night stay in Florence before or after the road trip.

You may also want to spend a few nights in a Tuscany villa with a private pool, perhaps at the end of your Tuscany road trip, to really soak up some relaxation before you leave!

I won’t cover any attractions or activities in Florence in this article, but you can find a dedicated post about the best landmarks in Florence and a three-day itinerary to discover the Tuscan capital.

You can combine them in any way that makes sense for your trip!

Day 1 of Your Tuscany Itinerary: Florence to San Gimignano

Leave Florence, with an optional stop at Castello di Poppiano.

External view of the medieval castle of Poppiano on the Via Chiantigiana
Make an optional stop at the Castello di Poppiano – but reserve a tour ahead of time!

Start your trip around the gorgeous Tuscan countryside in the morning, bright and early so that you don’t miss out on any of this trip’s glory!

The first day of your road trip in Tuscany is dedicated to exploring the picturesque Via Chiantigiana.

This scenic road unfolds through the undulating hills and vineyards known for producing the grapes for the famous Chianti wine, and it’s an exquisite start to your road trip.

As you drive out of Florence, you can have an optional stop, but it requires a prior reservation, so be sure to look into it before starting your trip. Check the website here.

Roughly 45 minutes from the center of Florence, Castello di Poppiano is a medieval castle belonging to the Guicciardini family since the late 12th century.

Amazingly, the family still owns the castle, passed down through the generations, and now they run guided tours with wine and olive oil tastings — delicious.

If you wish to join a tour of Castello di Poppiano, make a reservation at least two days before.

You can choose between a shorter one-hour tour and a longer two-hour one that includes access to the tower terrace and a bigger tasting with wine, oil, and food.

I do suggest the two-hour tour if you can make it work, but if you don’t have time, one hour is okay, or you can skip this stop entirely.

Head to Greve in Chianti.

The charming village of Greve in Chianti in the Tuscany region of Italy, with green hills in a lush part of the year
Stop in Greve in Chianti for a tasty lunch.

After your visit to Castello di Poppiano, make your way to Strada in Chianti, where you’ll join the Via Chiantigiana (SR222).

Drive south along the picturesque road for about 15 minutes to reach your next stop, Greve in Chianti.

A popular stop along the Via Chiantigiana, Greve in Chianti is a cute town where you can stop for a walk around, and enjoy a delicious lunch.

Where do I recommend? Depends on what you want, but Ristorante Pizzeria La Cantina is a popular stop for tasty pizza or traditional Tuscan dishes served with a glass of Chianti.

Move on to Castellina in Chianti.

The stone facade of the Church of San Salvatore in neo-Romanesque architecture style, located in the heart of Castellina in Chianti in Tuscany
Spend the afternoon exploring the charming Castellina in Chianti.

After lunch, continue driving south to the next town on Via Chiantigiana, Castellina in Chianti.

In the small historic center, visit the lovely Church of Saint Salvador and the Archaeological Museum of the Chianti Area.

Note that the museum is closed between January and March and only opens on certain days in November and December.

The area around Florence in winter does shut down a bit, so keep that in mind if planning an off-season road trip to Tuscany.

Make a brief stop in charming Poggibonsi.

panorama in the old town of Poggibonsi, italy, in the town square with a spire, clock tower, church, and other old historic buildings on the piazza
Make a brief stop in Poggibonsi en route to San Gimignano.

Your next stop before your final destination for the day is the town of Poggibonsi, less than half an hour from Castellina in Chianti.

The town is an important stop along the Via Francigena pilgrimage route and has a rich history dating back to the Neolithic period.

Stroll around the old town, check out the medieval Castello della Magione, and visit the Fortezza di Poggio Imperiale.

The town is small but charming, so you only need about one hour — that’s enough to check out the main sights before moving on to your final destination of the day, and settling in for some well-deserved rest at your hotel.

End the day in lovely San Gimignano.

view of the city of san Gimignano with its medieval stone towers protruding from the rest of the skyline of the hillside town
The medieval town of towers, San Gimignano is your final destination today.

Finally, drive to San Gimignano, one of the most picturesque towns in Tuscany.

This town is known for its wine production and charming streets, but it’s even better known for its many towers — 72, if I want to be precise.

Aim to arrive before sunset so you can climb one of the towers and enjoy a spectacular view from above!

Torre Grossa is the tallest in the town, but the effort to climb its many stairs will reward you with the best views.

For a different, less crowded option, you could alternately pay a visit to the twin towers, Torri dei Salvucci.

Other popular landmarks in San Gimignano are the iconic squares Piazza della Cisterna and Piazza del Duomo, great people watching spots in town.

In terms of landmarks, make time to visit the Duomo Collegiata di Santa Maria Assunta as well as the history museum, Tower and Casa Campatelli.

Visit all the attractions you can in the afternoon before heading for dinner: I recommend Ristorante Bel Soggiorno or Ristorante San Martino 26.

Since you’ll be sleeping in San Gimignano, you may leave some things for the following morning, before continuing your road trip.

Day 2 of Your Tuscany Itinerary: San Gimignano to Siena

Finish up in San Gimignano and (optionally) make a visit to Certaldo.

Tuscan medieval village of Certaldo Alto in the province of Tuscany, with orange buildings and brick road and historic towers

Spend the morning of your second day exploring the sights you didn’t get to see in San Gimignano.

However, be sure you leave a few hours before lunchtime so that you’ll have enough time for this jam-packed day ahead.

For the first stop of the day, the town of Certaldo, you’ll need to backtrack north for roughly 20 minutes… but I promise it’s worth it!

If you’d rather spend more time in San Gimignano, you can skip this stage and start driving later to the next attraction, Volterra.

If you choose to visit Certaldo, you’ll be rewarded with the picturesque sights of its medieval center, located in the upper town.

Catch the funicular to reach the upper town, and visit the main landmarks, including Palazzo Pretorio and Chiesa dei Santi Jacopo e Filippo.

The medieval town of Certaldo is also home to Boccaccio’s house, the birthplace of Giovanni Boccaccio, famed author of the Decameron.

The house is now a museum and offers lovely views of the Tuscan countryside.

Head to Volterra for lunch.

The stone walls and terra cotta roofs of Volterra Italy, in the Tuscan countryside, a must-stop on this Tuscany road trip itinerary

Whether you visited Certaldo or chose to spend extra time in San Gimignano, either way, next we’ll head to the town of Volterra.

The hilltop Tuscan town features well-preserved Etruscan walls around its gorgeous medieval center.

The landmarks you shouldn’t miss are the Cathedral of Santa Maria Assunta, the 13th-century Palazzo dei Priori, and the Roman Theatre.

Wander around Volterra’s picturesque alleys and charming squares and stop for lunch.

Try delicious sandwiches at La Sosta del Priore or enjoy a traditional Tuscan meal at La Taverna della Terra di Mezzo.

Head to Chiusdino and its famous abbey.

General view south side of the magical ruins of Saint Galgano Abbey, in the springtime with lush grass and trees
Don’t miss the abbey ruins outside of Chiusdino!

After lunch, drive to Chiusdino, another delightful Tuscan village with a compact but beautiful medieval town.

Explore the small village and visit the Church of San Michele before continuing your drive toward Siena.

An optional stop just outside Chiusdino is the Abbey of Saint Galgano.

This Gothic-style 13th-century abbey stands roofless in the middle of the Tuscan countryside. The abbey is close to the road, so it’s easy to stop by for a short visit.

Head to Siena to end the day.

View of the famous striped facade of the church in Siena as seen from a rooftop terrace area as an aerial view over the city

Finally, drive to Siena, where you can spend one or two nights, depending on how much time you have reserved for this Tuscany itinerary.

The city is full of amazing landmarks, so you can easily spend more than one day exploring its main sights.

Nevertheless, if you’re short on time, you can check out the most important landmarks in just half a day, if you have to.

Keeping this as just a half-day stop would keep this as a 5-day Tuscany itinerary, but if you spend another day in Siena, that will make this a 6-day road trip.

If time is short, spend the rest of your afternoon and evening exploring the historic center of Siena, revolving around the iconic Piazza del Campo.

The imposing Gothic-style Palazzo Pubblico and the iconic Torre del Mangia tower over Piazza del Campo, and both are must-visits even if you have a short time in Siena.

Just a few minutes away, in Piazza del Duomo, you’ll find the Romanesque-Gothic Duomo di Siena known for its striped marble façade — one of the most beautiful churches in Italy, which is high praise.

End your evening in Siena with a traditional dinner at Osteria Il Carroccio or Osteria degli Svitati, both serving delicious Tuscan dishes.

(Optional) Additional Day of Your Tuscany Itinerary: Siena

Explore the town of Siena, on your own or with a tour.

Palazzo Pubblico's gothic facade with archways, red stone, and a large campanile bell tower with a clock on it, in an empty piazza
If you can swing it, spend an extra day in Siena!

If you decide to spend a second day in Siena, there are plenty of landmarks to explore and activities to do.

You can take advantage of the fact that you won’t be driving and go on a wine-tasting tour.

Choose between staying in Siena and joiniing a local tour like this Siena: Food and Wine Walking Tour or exploring the nearby countryside on this half-day Educational “Vine, Wine, & Life” Tour & Tasting.

Spend the rest of the day exploring Siena and visiting more beautiful landmarks.

In Piazza del Campo, climb to the top of the Tower of Mangia for sweeping views of Siena’s historic center.

The climb up the 87-meter tower can be challenging, but the view is one of the best in town.

Another cool observation point is the so-called Facciatone.

You’ll climb on top of the façade of what was supposed to be an additional nave to the Duomo di Siena but was never completed.

The incomplete project is now known by its literal term, Facciatone, meaning big façade.

Aerial View of Duomo di Siena from Facciatone
An epic view of Duomo di Siena from Facciatone!

Outside the historic center, visit the 16th-century Fortezza Medicea to enjoy the view of Siena from a distance.

Not far from the fortress, the Basilica Cateriniana San Domenico houses several relics of Saint Catherine of Siena, the patron saint of Italy, together with Francis of Assisi.

The most important relic is the saint’s mummified head — creepy but very cool, as long as you don’t mind a little macabre sightseeing!

These landmarks and activities should keep you busy for a whole day in Siena, but if you have extra time and you enjoy visiting museums, you can check out the museum of Santa Maria della Scala, housed in a former hospital.

For your last dinner in Siena, check out the scenic SaporDivino Restaurant or the beautiful terrace of Ristorante Tar-Tufo.

Spend one more night in Siena before you continue your Tuscany road trip.

Day 3 of Your Tuscany Itinerary: Montalcino to Montepulciano

Make your way to Montalcino.

The ancient Italian town of Montalcino, view as seen from the city tower.

From Siena, start driving south toward the small town of Montalcino, better known for its signature wine, Brunello di Montalcino.

On the way, you’ll pass through Buonconvento, another lovely town with a small but charming historic center.

Park the car and go for a short walk along the few narrow streets that make up the little town.

Roughly 20 minutes south of Buonconvento, you’ll reach Montalcino.

The hilltop town offers panoramic views of the surrounding Tuscan countryside, one of the best views you’ll see on this Tuscany road trip.

The best views are from the Fortress of Montalcino, a 14th-century fortress at the highest point in town.

Medieval fortress of Montalcino, Tuscany, one of the places to stop in this historic Tuscan village

You can walk all around the fortress walls for a small fee and even check out a wine shop inside.

The small medieval center of Montalcino has other beautiful viewpoints and a few more landmarks worth visiting, including the Palazzo dei Priori and the Cathedral of the Holy Savior.

If you’re looking to buy a bottle of Brunello di Montalcino, you’ll find many wineries and wine shops in town to bring home this delicious Tuscan souvenir!

Make a stop at the Val d’Orcia Scenic Spot.

Panoramic view of a farmhouse near Asciano with Val d'Orcia hills in the background.

From Montalcino, you’ll head to Pienza… but not without making a stop at one of the most famous photo spots of Tuscany!

You’ll need to drive for about half an hour to the east to reach Pienza, one of the most beautiful towns of the Val d’Orcia, and your stop for lunch.

But first, plug in Val d’Orcia Scenic Spot to your Maps app or navigation device — this is where you’ll want to stop for that iconic photo of Tuscany that may have inspired this trip in the first place!

Head onwards to Pienza.

the charming old town of pienza italy with red stones and trees and church

Once you reach Pienza, it’s time for lunch — your stomach is probably growling at this point.

In the charming Piazza di Spagna, the cozy osteria Sette Di Vino serves heartwarming dishes in an old-fashioned setting.

After lunch, explore the small historic center of Pienza and visit the Pienza Cathedral (Duomo di Santa Maria Assunta) and the beautiful Palazzo Piccolomini.

Near the cathedral, you’ll also find a few viewpoints to admire the rolling Tuscan hills stretching in the distance.

End the day in Montepulciano.

Palazzo Comunale (Town Hall) in Piazza Grande, Antique Montepulciano town
End the day in Montepulciano – wine tasting and exploring!

Finally, drive to your last stop for the day, Montepulciano.

Like many towns in the region, Montepulciano also gives its name to a wine variety, so a wine tasting is in order!

Once you reach Montepulciano, you’ll be done driving for the day, so you can relax, explore the town, and check out one of the many wineries.

De’ Ricci Cantine Storiche is smack in the historic center of Montepulciano and offers great tours of their cave cellars, along with wine tasting. You can join the wine tasting before or after exploring the town.

A few sights you shouldn’t miss are the gorgeous Fortezza Medicea and the Piazza Grande.

The famous piazza is encircled by impressive buildings like the Palazzo Nobili-Tarugi, Palazzo del Capitano del Popolo, and the Cathedral Saint Mary of The Assumption — all worthy of a stop!

End the day with a delicious dinner in Montepulciano before heading to your hotel for a good night’s sleep.

I recommend Rosso Rubino Trattoria and La Pentolaccia: two great options for genuine local dishes that use the flavors and ingredients of the region.

Day 4 of Your Tuscany Itinerary: Chianciano Terme to Arezzo

Make a brief stop at the Sanctuary of the Madonna.

San Biagio, a Renaissance Greek cross central plan church outside Montepulciano

Start your second to last day of the Tuscany road trip by visiting the Sanctuary of the Madonna di San Biagio, just outside Montepulciano.

A gorgeous example of Renaissance art, the sanctuary is a must-see for anyone passing by Montepulciano.

For a small fee, you can admire the beautiful artwork inside the church and get an audio guide.

Head to Tuscany’s beloved thermal baths.

Steam rising from hot springs in Theia Thermal Baths in Tuscany
The Theia Thermal Baths are a nice place to pause, soak, and restore. Photo Credit: Stefano Cannas via Flickr (CC BY-NC 2.0)

Next, drive to Chianciano Terme for a relaxing time at the stunning thermal baths in town.

The Theia Thermal Baths feature four outdoor pools and three indoor ones with thermal water coming from the Sillene spring, so long known for its beneficial properties that it’s been used since the Etruscan times!

Reserve your access to the thermal baths in advance and enjoy a few hours in the pools overlooking the Tuscan countryside, relax in the sauna, and maybe get a massage in the wellness center.

You can stay for lunch at the on-site restaurant or drive to your next destination.

Make your next stop in Cortona.

The wide staircase leading up to the Cortona Cathedral in the heart of the old historic town of Cortona

Less than one hour north of Chianciano Terme, Cortona is another delightful town known for its Etruscan heritage.

If you’re a history geek, the Accademia Etrusca is a great spot to learn about the town’s history and admire Etruscan artifacts.

The historic town of Cortona is full of beautiful churches, including the Cortona Cathedral and the small Church of St. Nicholas, jam-packed with beautiful paintings.

Around the main town square, Piazza della Repubblica, you’ll find charming historic buildings and many restaurants.

If you didn’t eat at the springs, you can stop here for lunch at the cozy Osteria del Teatro, a place I highly recommend.

End the day in Arezzo.

the main square Piazza Grande with the medieval church and buildings, in the old town of the ancient Italian city of art, Arezzo

After exploring Cortona, it’s time to drive to Arezzo, where you’ll be spending the last night of your road trip around Tuscany.

On a hill in the eastern part of Tuscany close to its neighboring region of Umbria, Arezzo was an important city for the Etruscan civilizatio, until it was later conquered by the Romans.

The city is best-known for its medieval churches and buildings and the ever-present Medicean Fortress.

The top sights in Arezzo are the medieval Arezzo Cathedral and San Francesco Basilica, two must-visit religious sites.

If you want to keep exploring, visit the National Museum of Medieval and Modern Art, people-watch on the gorgeous Piazza Grande, and of course spend some time enjoying the Fortezza Medicea with its surrounding park.

To end a full day of activities and exploring, enjoy a tasty dinner at Teorema del Gusto or Il Covo dei Briganti, then spend the night in Arezzo.

Day 5 of Your Tuscany Itinerary: Arezzo to Florence

Stop at the little town of Anghiari.

The charming village of Anghiari near Arrezzo with cobblestone and stairs

On your last day exploring Tuscany, it’s time to drive back to Florence, but not before exploring two more gorgeous Tuscan towns on the way.

Your first stop is the charming town of Anghiari, only half an hour from Arezzo.

Anghiari is famous for being the location of an important battle between Florentine and Milanese troops in 1440, back when Italy was divided into several states.

The battle was later meant to be depicted on a mural in the Palazzo Vecchio in Florence by Leonardo da Vinci, but he never completed it.

You can learn more about the battle and the town’s history at the local museum, Museo della Battaglia e di Anghiari.

Wander for a while around the small medieval center and along the old town walls (N’tra Le Mura D’Anghiari) to enjoy beautiful views and check out the charming squares, medieval buildings, and beautiful little churches.

Make a final stop in Poppi before returning to Florence.

Poppi medieval village and castle panoramic view on a beautiful spring day

After visiting Anghiari, drive for around one hour north to reach the last town on this Tuscany itinerary, the picturesque Poppi.

The town is home to the medieval Castle of the Earls Guidi, the beautiful Church of San Fedele, and the Monastery of Camaldoli.

If you choose to have lunch in Poppi, you should try the delicious, heartwarming cuisine of La Taverna del Castello, right in the town center.

After lunch, start driving back to Florence, roughly one hour and a half from Poppi.

In Florence, you can leave your rental car and, if you have extra time, spend a few more days visiting the many landmarks and museums of the Tuscan capital.