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.
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.
The Most Beautiful Towns in Tuscany
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.
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 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.
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.
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.
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.
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
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.
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.
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.
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.
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.
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.
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
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.
Roxana is a Romanian-born freelance travel writer who has lived in Italy for over 15 years. She has a Master’s in Journalism and a Bachelor’s in Film Studies. Her mission is to find hidden gems, even in the most popular travel destinations, and to inspire people to explore new places and cultures with the same curiosity! When she is not traveling, writing, or planning her next trip, she is either binge-watching TV shows or reading books.