Trip Itineraries

Ah, Puerto Rico. It is appropriately called “La Isla del Encanto” — in English, the Island of Enchantment.

This small Caribbean island is vibrant and truly enchanting with its stunning beaches and wonderful people. Puerto Ricans are welcoming, lively, and resilient.

Puerto Rico is not always an easy place to live — scars from hurricanes, colonization, and poverty will tell that story — but it is a beautiful one.

Above all, Puerto Rico is alive. You will find incredible street art and the rumble of music on the streets of San Juan. You will be amazed as you snorkel above magnificent coral reefs with colorful fish darting below. The food is delicious, especially for fans of mariscos (seafood), plantains, and tropical fruits.

While Puerto Rico is a beautiful place, there is quite a complex history. While we can’t cover the subject with any hope of comprehensiveness in a short blog post like this one, we’ll quickly try to introduce it.

PLANNING FOR PUERTO RICO AT A GLANCE:  

When to Go: Puerto Rico has a beautiful tropical weather almost throughout the entire year but it's between December and April that it shines the most. 

It's perfect for relaxing on the beach and participating in other major activities, this is Puerto Rico's high season so you can expect prices to be high. 

If you want to beat the crowds and pay a bit less, then you can consider visiting between mid-April to June. Avoid late summer as this is hurricane season.

Where to Stay: Puerto Rico is beautiful on every turn but for this itinerary, I recommend staying in these areas —  San Juan, Fajardo, and Vieques. 

In San Juan I recommend staying at Dorado Beach Ritz-Carlton for a luxurious experience, O: Live Boutique Hotel if you love Mediterranean-inspired details and Nomada Urban Beach Hostel for budget travelers. 

When in Fajardo, I suggest staying at a private villa at the Rio Mar Beach Resort if you love staying in villas, St. Regis Bahia Beach Resort for a luxurious stay in a resort-style hotel, or Surfing Turtle Inn if you're looking for a budget-friendly hostel.  

In Vieques, opt for Finca Victoria for a boutique eco farm stay, Tranquility by the Sea for a seaside cottage, and Lazy Hostel for a budget-friendly hostel.

How to Get Around: While driving in Puerto Rico can be a bit tricky (especially for nervous drivers) since drivers can be a bit aggressive here, I think it's worth it. I like the freedom that comes with deciding where and when to make a stop without feeling rushed or delayed. 

Alternatively, you can choose to take tours but that can get expensive pretty fast. If you do choose to rent a car, compare car rentals and prices from here. 

Best Activities: Don't want to drive or plan? Booking a few different activities can help you eliminate the need for driving around. You can book a food tour, a craft rum cocktail tour, or Old San Juan Sunset Cruise.

3 Things Not to Forget to Pack: Since you'll spend plenty of time on the beach, I recommend taking this Dock & Bay travel towel which is 100% made from recycled materials. You'll need a swimsuit to fully enjoy the beaches -- this is my favorite swimwear  -- and of course sunscreen -- I love SunBum SPF 50 with Vitamin E — it’s moisturizing and soothing for you and also harmless for marine life! 

A Quick History of Puerto Rico

The island that is now known as Puerto Rico was originally inhabited by the Taíno people. Their name for the island was Borikén, which meant “land of the brave lord”, in their native tongue, Arawak.

Today, many Puerto Ricans identify themselves as “boriqua”, the adjective deriving from the land’s original name. When you consider the fact that Puerto Rico translates to “rich port” in Spanish, you can see how the Spanish saw the land: a place to be conquered and looted, rather than respected.

Unfortunately for the Taíno people, Christopher Columbus made his way to Puerto Rico in 1493. Like many other Caribbean nations, the Taíno way of life was changed drastically by this unwelcome arrival. Columbus placed the island under an encomienda system, similar to the feudal systems of Europe, which essentially enslaved the Taíno people on their own land, forcing them to work in gold mines and on plantations.

The Taíno population quickly started declining due to the introduction of European diseases that never existed on the island previously, such as smallpox, measles, and typhus, as well as through the harsh conditions of slavery.

Who remained of the Taíno people were subject to cultural genocide practices, such as the Complementary Declaration of July 28th, 1513, which “freed” only the Taíno who were “clothed, Christian, and capable”, further chipping away at Taíno identity.

By 1530, the effect of 40 years of European colonization had taken an enormous toll. The original population of an estimated 50,000 Taíno dwindled down to just 1,148 survivors in the 1530 census. The remaining Taíno were still oppressed, and many Taíno women intermarried with the Spanish conquistadors and assimilated.

There’s no denying that the Taíno people as a distinct Indigenous group are a shadow of what they used to be. However, Taíno blood runs in the veins of many Puerto Ricans, and Taíno identity is being shaped and defined by the descendants of these Indigenous people living today.

There are ancient sites all over the island to visit and honor these unforgotten people. There are a few towns in Puerto Rico that still retain their Taíno names: for example, Yauco and Utuado.

After over 300 years of Spanish colonization, the United States claimed Puerto Rico in the Spanish-American War in 1898. Today, the questions of statehood and Puerto Rican independence are thorny ones, and the path forward for Puerto Rico is not entirely clear.

Today, many Puerto Ricans call the island Borinquen, to honor their Taíno roots and acknowledge the Taíno, Caribbean, African, and Spanish influences on the island’s ethnicity and culture in a way that is more inclusive than the Spanish-given name of Puerto Rico.

How this Puerto Rico Itinerary Works

Now that you have a bit of knowledge of the history of the island, let’s get into the nitty-gritty of this Puerto Rico itinerary.

The following suggestions only cover a small portion of the east side of the island, since this itinerary only covers 7 days in Puerto Rico.

We’ve highlighted all the most popular touristic hotspots in Puerto Rico and given some off-the-beaten-path suggestions where it makes sense to best maximize the time on your trip to Puerto Rico.

However, if you have more than a week in Puerto Rico, we strongly suggest you make your way around the entire island; you will be amazed at the variety of climates. Explore desolate salt flats, lush rainforest, coral reefs, mountain waterfalls, lakes, and countless beaches that would make a postcard weep.

What to Pack for Puerto Rico

I’m in the process of creating a full Puerto Rico packing list, but here are 5 things not to forget before your trip.

An awesome travel towel. A proper travel towel is a game-changer. I’m not talking about a sad little microfiber square that might as well be a washcloth. I’m talking a true microfiber beach towel that serves you just as well on a beach day as it does after a long shower. I’m obsessed with this classic red and white striped travel towel from Dock & Bay, which easily knocks off sand in a single shake-out and is made of 100% recycled materials. Order it on Amazon here.

Bathing suits you love. On an island trip, you’ve got to have swimwear you can stand behind! I love wearing a two-piece, but I hate feeling bloated while I travel and feeling awkward in my swimwear after too much mofongo. Solution? High-waisted swimsuits! I love this one, and this one is a great plus-size option with a high waist and a classic shape. I would bring 3 swimsuits for one week in Puerto Rico so I never have to suffer the indignity of putting on a wet bathing suit. Ick.

Reef-safe sunscreen. This is so essential! The future of marine life in Puerto Rico depends on the actions visitors and locals take now, so do your part to keep Puerto Rico’s reefs pristine for generations to come. I love SunBum SPF 50 with Vitamin E — it’s moisturizing and soothing for you, and harmless for the animals who call Puerto Rico’s waters their home!

Comfortable travel sandals. I will be buried with my Birkenstocks, or you can try to pry them from my cold, dead hands. Dramatic? Maybe. But they’re a must for travel! I love the Birkenstock Gizeh leather thong style personally, but the classic two-buckle Arizona slides are really cute as well. These are the exact shoes I have and love!

One tip, though: Break them in for 2-3 days before you travel, as they form to the exact shape of your foot! They’ll be slightly uncomfortable at first, but nothing major (I just bought a second pair and they fit like a glove after a day of use), but they’re not shoes I’d want to walk around a cobblestoned city in on their first day!

Chemical-free insect repellent: Like reef-safe sunscreen, it’s important that the bug spray you use won’t harm the sensitive ecosystems of Puerto Rico, particularly when you get in the water! A simple lemon eucalyptus spray like this will keep most mosquitos away without the harsh chemicals which can mess up delicate ecosystems.

Where to Stay in Puerto Rico

This Puerto Rico itinerary has you staying overnight in three separate destinations: San Juan, Fajardo, and Vieques. We’ll give you some suggestions for each!

San Juan

BOUTIQUE | I love the Small Luxury Hotels of the World brand and I’ve stayed at many a property of theirs over the years! They have a gorgeous offering called O:Live Boutique Hotel located in vibey Condado that I’m looking forward to staying at on my next trip to the island! Gorgeously designed rooms with Mediterranean-inspired details, rain showers with hydromassage jets, a roof terrace with an infinity pool with views of the Condado Lagoon? Swoon. Sold.
>> Check availability and rates on Booking.com

LUXURY | Nothing says luxury quite like the Ritz-Carlton brand! At Dorado Beach Ritz-Carlton, we’re talking on-site golf course, multiple swimming pools, 4 on-site restaurants, and spa and fitness centers. Plus, some rooms even have their own private plunge pools for the ultimate luxury vacation! It’s not cheap, that’s for sure, but it’s by far the best choice if you’re looking for a blowout accommodation choice for a special occasion (or just a really baller vacation).
>> Check availability and rates on Booking.com

BUDGET | Looking for a hostel option? Nomada Urban Beach Hostel is a fantastic choice for travelers on a budget, located near Isla Verde Beach. Options include dorm-style rooms and private rooms. The dorms are modern with amenities like curtains and hangers allotted for each bunk bed: little touches that frequent hostel-goers are sure to heave a sigh of relief over. There’s also a roof terrace for travelers to relax on and chitchat.
>> Check availability and rates on Booking.com

Fajardo

VILLA | If you want to stay in a villa, there are some great choices in this area! This charming private villa at the Rio Mar Beach Resort in nearby Rio Grande is a great choice for people who want to spread out and enjoy a larger space without paying a huge price. It can sleep up to six guests in its one bedroom, two sofa bed configuration. The villa also has two bathrooms, a full-size kitchen and dining area. It’s not fancy, but it’s spacious and charming.
>> Check availability and rates on Booking.com

LUXURY | If you want resort-style luxury, the St. Regis Bahia Beach Resort is a phenomenal option about 12 miles north of Fajardo. Amenities include a golf course, ocean-view pool, spa center, yoga and pilates classes, and best of all? Every room includes butler service for that special ultra-luxury touch, plus either gorgeous garden or ocean views.
>> Check availability and rates on Booking.com

BUDGET | For a cute hostel experience, go outside of Fajardo 5 miles to Luquillo, a charming beachy area with lots of great food. The Surfing Turtle Inn offers dorms and private rooms at affordable prices for the area. Dorms and rooms are fairly basic, but offer all the standard budget amenities at a reasonable price, with a clean reputation.
>> Check availability and rates on Booking.com

Vieques

BOUTIQUE | Eco-friendly and chic, Finca Victoria is the place to go for a stunning, Instagrammable retreat-style hotel at an affordable cost. It has beautiful treehouse-inspired rooms with soaringly high ceilings and exposed beams, loads of natural light, and vintage farmhouse details in the furnishings. Daily free yoga classes are included, as well as a delicious Caribbean breakfast made with Ayurvedic principles in mind. There are loads of thoughtful touches like hammocks on the balcony, outdoor showers, and small kitchenettes.
>> Check availability and rates on Booking.com

COTTAGE | The lovely Tranquility by the Sea offers a 3-bedroom oceanside cottage perfect for families and groups at a good value. It’s not fancy, but it is well-appointed and spacious with plenty of room to enjoy a vacation home style rental. A full kitchen, washer & dryer, and a wraparound veranda are some of the best perks of this rental. Best of all? You can often see wild horses grazing right from your window.
>> Check availability and rates on Booking.com

BUDGET | While the decor is definitely nothing to write home about, if you want a cheap and clean place to lay your head at night, Lazy Hostel is a good choice. It has a social vibe and it offers a variety of room types including dorms and private rooms. It’s good for solo travelers and anyone on a budget in Puerto Rico.
>> Check availability and rates on Booking.com

A Few Final Tips About Visiting Puerto Rico

A few quick tips before you arrive on the island!

Cell service can be spotty. So make sure you download maps of the areas you are in to be sure you can find your way. That means you should also keep your phone charged.

Google Maps are not always accurate either. I try to cross-reference with Maps.me and always check my accommodations or destinations to see if they have alternate directions.

Anti-theft bags are great for San Juan. While Puerto Rico is overall safe, San Juan is a large city like any other, and you should use caution. When traveling in cities, I bring my PacSafe CitySafe backpack — it’s chic, sleek, and almost theft-proof, with things like double-locking zippers and mesh slash-proof construction.

The driving in Puerto Rico can be wild. If you’re not used to it… watch out! The right lane is the fast lane, the left lane is the slow lane, and merging onto highways via the right lane is practically a form of cardio. While renting a car in Puerto Rico will give you freedom, it can also be stressful. I suggest a handful of guided tours on this Puerto Rico itinerary so that you can reduce your driving and focus on relaxing, while also having your adventure improved by local guide knowledge.

Watch for mosquitos. Puerto Rico has a tropical climate and therefore a handful of tropical diseases you don’t have to worry about in most of the U.S. mainland. Dengue fever, Zika, chikungunya, and other diseases are transmissible through mosquito bites. Wear mosquito repellent during day and night, and be especially careful around sunrise and sunset, when mosquito activity is at its peak. Reapply and wear long-sleeved, loose-fitting clothing at this time for the most coverage.

To Rent or Not to Rent?

We’ve done a lot of the hard work for you in putting together this itinerary for Puerto Rico, but there’s one big decision you need to make: to rent a car or not to rent a car?

As I mentioned above, driving in Puerto Rico can be difficult. Drivers are a bit on the aggressive side, and the fact that the right lane is the fast lane and the left lane is the slow lane can be a real mind#(*@ for anxious drivers like myself.

I’ve been to Puerto Rico twice, once without a rental car and once with. I was able to adjust to the driving, but there were definitely some heart-pounding moments! Ultimately, I liked the freedom it gave me, though I didn’t enjoy driving on the tiny streets of Old San Juan.

There are tours and taxis you can take which make having a car unnecessary; plus, you ought to leave your rental behind when you go to Vieques, as the car spots on the ferry are limited and are needed by locals. Plus, many rental companies do not allow it.

However, tour and taxi costs can add up, so you’ll want to do some cost benefit analysis there. Renting a car likely skews cheaper, but it will mean some headache. Tours and taixs will likely skew a bit more expensive, but be more relaxing.

If you do choose to rent a car, there are ways to get a good deal on your rental. I’ve rented cars dozens of times through various search engines and have settled on Discover Cars as the best car rental search engine – it searches over 500 trusted rental companies to find the cheapest price for your rental! Compare prices for car rental from San Juan Airport here.

Puerto Rico Itinerary: 7 Days on the Island of Enchantment

Day 1: Explore Old San Juan

Old San Juan is one of the most lively areas of the islands!

The colorful and stunning architecture reflects the early days of San Juan shortly after the arrival of the Spanish conquistadors, and some of the earliest buildings dating back to 1508. 

The historic forts and old city walls are especially impressive. Beyond the architecture, San Juan has some of the best eating in Puerto Rico, so bring your appetite!

Start your day off with a cup of coffee.

You’re in Puerto Rico, so it’d be a shame to start the day without a proper café con leche. Puerto Rico is full of coffee farms so be prepared for fresh, delicious coffee that’s local and delicious.

To indulge your coffee craving, head to Cuatro Sombras. This is the coffee house of choice if you are looking to try locally-grown coffee. Enjoy shade-grown coffee from the mountains of Yauco in El Yunque National Park.

Their food menu includes pastries, breakfast plates, sandwiches, and paninis. It is the perfect place to start the day and fuel up with some locally grown coffee.

But resist the urge to overindulge here — next up on this Puerto Rico itinerary is enjoying a delicious walking food tour to get a sense of Puerto Rican flavors.

Taste the flavors of Old San Juan.

On my first day in a destination, I love to do a food tour for a variety of reasons. For one, it’s a great way to learn what you like and what you don’t — as well as what you haven’t sampled yet! — so you can order tastier and more adventurous dishes on your travels.

It’s also a great way to ask a local for their point of view on the best restaurants in San Juan, so you can plan future meals and make sure you don’t miss out on any can’t-miss foodie experiences.

This highly-rated food & walking tour will provide you with the opportunity to enjoy Puerto Rican cuisine and do some more coffee tasting. Plus they provide a cocktail, if you don’t mind imbibing on the early side (you are on vacation, after all!).

This tour will take you through the streets of San Juan while you admire the architecture and learn about the history of this colonial city and how San Juan came to be. It is a well-rounded (and delicious) Puerto Rican cultural experience and a great way to start off a weeklong Puerto Rico itinerary.

Book your food tour online here!

Relax on the beach in Condado or Isla Verde.

From there, you may want to rest your legs for a bit and relax on the beach and digest all that delicious Puerto Rican food!

Head to Condado Beach to experience the beach, enjoy the view, and relax…. plus there is a lot of shopping in Condado for those wanting to explore more and find some Puerto Rican souvenirs to take home.

However, Condado Beach is in one of the most built-up areas of San Juan. If you would like a more laidback Puerto Rican beach experience, head to Isla Verde Beach, otherwise known as Playa Isla Verde in Carolina.

There are multiple bars and restaurants along the beach here which is how it is done at many popular beaches in PR!

Enjoy San Juan at night one of three ways.

No matter what you choose, you’ll want to eat a big dinner before you explore more of San Juan. This choice is up to you. Both Condado and Isla Verde provide plenty of opportunities to eat well, or perhaps your food tour guide gave you a can’t-miss recommendation for where to eat. If they did… heed it!

There are a few different things you can do to cap off your first night in Puerto Rico. One suggestion is to take a craft rum cocktail tour, to learn why Puerto Rico is the rum capital of the world!

You will taste many delicious rum-centric beverages while exploring the colorful nightlife of Old San Juan. You will get to experience a variety of bars in the city and learn about the drinking culture of Puerto Rico. Get to know the city and its history while getting your buzz on!

Book your rum cocktail tour here!

It also must be said that viewing the forts at night is especially impressive! Walk from Castillo San Cristobal to Castillo Felipe del Morro. Enjoy the sound of the ocean while taking in the impressive view.

There are multiple historic citadels, old city walls, and forts in this area, representing the previous Spanish military presence in the former Spanish colony. Some of these looming structures date back to the 16th century and are in remarkably good shape for their age.

Add Paseo Del Morro to your night exploration to continue along on a boardwalk flanked with the city walls on one side and the bay on the other. It runs into Paseo de la Princesa which will allow for you to be able to do almost a full loop around the old city walls.

Day 2: Do it all in San Juan

Hopefully, you will wake up well-rested for another stellar day in San Juan! This is the last full day in San Juan on this PR itinerary, so let’s make the most of it.

I highly suggest you start the day with an early morning dive if you’re certified, or do some snorkeling. Then we’ll explore a bit more of San Juan to close out the day.

Start the day with a fantastic breakfast.

This means fueling up with something light like fruit or a pastry with some more local coffee before you hit the water.

Check out Cafe Cola’o. This is a woman-owned coffee shop that features coffee from Utuado, Adjuntas, and Ponce. Cafe Regina is another spectacular spot representing Puerto Rican agriculture. Sample starfruit jam, locally made ice cream, and excellent coffee.

Head to Escambrón Beach.

One of the best ways to get around the city and get the heart pumping is to rent an electric scooter. Skootel is a new app-based scooter rental service in PR. You can find it on the Bird app. The options are varied as to how you will want to take advantage of your scooter rental. 

Head to Escambrón Beach any way you like. We suggest a scooter, of course! You may want to head out and go the long way to view the forts again, this time by day.

Old San Juan is so small that any way you choose to get to the beach will be relatively fast and easy to navigate. It is, of course, very fast if you drive, if you were brave enough to rent a car.

Playa El Escambrón is a great spot to enjoy the beach for anyone not wanting to snorkel or dive. However, the shining star of Escambrón is the snorkeling and diving adventures that await you under the sea!

Be prepared for sea turtles, coral reefs, and calm waters. When you explore Escambrón Marine Park, you will find incredible sunken structures throughout.

Picture the columns of Atlantis, statues, and a sunken “fish protection wall”. This is a great spot to try scuba diving for the first time with its easy beach access and shallow waters.

Please remember to use reef-safe sunscreen any time you get in the water. The future health of the marine ecosystems of Puerto Rico is dependent upon it! I use and love SunBum SPF 50 with Vitamin E — it’s great for your skin and for the marine environment.

Have a delicious brunch.

After you have had your fill of the water, it’s time for one of the best brunches of your life!

You will be very pleased to refuel at Waffle-Era Tea Room. This place is the ultimate breakfast spot. They feature an extensive list of savory and sweet waffles, plus salads and bowls.

Of course, you can also enjoy an extensive tea menu! Think fragrant earl grey, peony, or lemongrass chai. There are all kinds of varieties of tea, plus there are mimosas, bloody marys, and cocktails…. it’s even encouraged to spike your coffee (hey, vacation, right?). It’s a grand reward after you have spent time in the water and sun!

Check out the beautiful shops of Old San Juan.

The afternoon will be your chance to check out some of the unique shopping experiences Old San Juan has to offer and support the local businesses.

One such location is at the enchanted library, called Quimera, Café Literario. You will mostly find books about spiritual development, fairy tales, and magic, though, this magical bookstore-meets-café is much more than that!

The Poet’s Passage is just down the way from Quimera. It is self-described to be a “living museum of poetry and local art”. This is certainly true. They also host spoken-word and music events, and because it’s Puerto Rico, land of delicious coffee, there is a café here too. 

Looking for a souvenir? Check out Seafoam for locally made rare jewelry. El Gapon hat shop is a great spot to check out, too.

Take a sunset sail.

As the day begins nearing a close, head on out for your sunset sailing tour!

The meeting place is between Pier 3 and 4 at San Juan Bay at 5:30 PM (though double-check as varying sunset times throughout the year may impact this).

Climb aboard the Amazing Grace, a sailing vessel dating back to the American Revolutionary War. Enjoy beverages, cocktails, and appetizers as you cruise San Juan Bay viewing historic buildings like La Fortaleza, the Governor’s mansion… plus you can enjoy local music aboard the vessel. The views are stunning on this small-group tour!

Be sure to wear comfortable shoes and bring your ID!

Book your tour here: Old San Juan Sunset Cruise

Have a delicious dinner.

After your happy hour aboard the Amazing Grace, it is time for dinner in San Juan. There are some world-class restaurants in San Juan ranging from upscale to casual fare of all kinds.

If you are looking for a casual experience, you should check out Lote23 in Santurce. This gastro park will provide you top-notch fare from some of the best chefs in Puerto Rico!

Each stand has something unique and bound to be mouth-watering. Enjoy mofongo (mashed green plantains) at El Cuchifrito or Puerto Rican pork shoulder sandwiches at Pernilería Los Proceres. Plus you will find poke bowls, fried chicken, cocktails, and more.

Head home early or continue the night out.

If you are looking for more to do after dinner you may want to experience the Condado nightlife.

Condado has the best nightlife scene on the island. There are many cool bars, lounges, and clubs. We love Oceano for its rooftop views and excellent outdoor seating, La Terraza for cheap margaritas and reggaeton, and Red Coral Lounge for the artwork and ambiance, especially the giant coral sculpture.

This is the spot if you want to go out dancing and stay out late… but be sure to get some rest. You have another jam-packed day ahead of you!

Day 3: Journey to the rainforest

Today is all about El Yunque National Forest, the only tropical rainforest in the United States! It’s an absolute must-visit on any Puerto Rico itinerary.

Getting to El Yunque by car is absolutely doable! It’s about a 45-minute or 1-hour drive, depending on traffic. However, Puerto Rico driving is not for everyone, so we’ve also vetted and suggested a tour that will show you around El Yunque stress-free.

Grab a tasty breakfast with a side of history.

Start the day off with a healthy breakfast steeped in history at St Germain, which is a great spot for vegetarians especially!

You will dine in a historic building that was once home to Don Pedro Albizu Campos, widely considered a hero in Puerto Rico.

He was the leader of the Puerto Rico Nationalist Party from 1933 to 1965, leading uprisings to overthrow the United States government. He was imprisoned for many years of his life. Dine at this restaurant and pay homage to the struggle that Puerto Rico has lived through due to colonization.

Head out to the rainforest.

Once you are satiated, it is time for your rainforest and waterslide tour in El Yunque National Forest! Yes, this tour takes you on natural waterslides — nothing manmade about them! We suggest going by tour, but we’ll also include how to get there on your own below as well.

It is an insanely awesome, one-of-a-kind adventure. It is not every day you get to experience this! Plus you can cliff jump, rope swing, and bask beneath waterfalls. There is also a stop at a restaurant on this tour where you can Puerto Rican cuisine.

Book your El Yunque Rainforest & Waterslide Tour!

If you have rented a vehicle, you can make this trip without a tour. You will want to head to Las Pailas in Luquillo. There is a $5 parking fee. The lot is in a local’s yard at these GPS coordinates: 18.337856, -65.731060.

Follow the path from the parking area down to Río Pitahaya where you will venture to find the two waterslides.

Once you have exerted yourself head over to La Muralla, located nearby, right in El Yunque. Get simple, delicious Puerto Rican food and fresh coconut water to recharge before you head back towards San Juan for dinner.

Walk around San Juan a bit before dinner.

Before dinner, you may have some time for resting, or you can tour more of San Juan.

One fun way to see the city is to do a DIY mural tour, as there are plenty of thought-provoking, electric murals in this city. You will get a modern idea of what is happening in PR by observing the artwork of real Puerto Ricans.

Dine at one of San Juan’s best restaurants.

The dinner options in San Juan are endless! If you want to dine near the water, La Casita de Rones is the place. They have great food and craft rum cocktails. The restaurant is close to where the cruise ships dock, though, so it can get very busy: be warned!

El Jibarito is a great place to go if you want to try one of Puerto Rico’s national dishes, mofongo. Mofongo is a dish consisting of mashed green plantain and broth.

The plantain is mashed to the inside of the bowl where they pour in various types of broth. It can be made with beef, chicken, seafood, or creamy broth, and then it’s typically served with meat or seafood inside.

Whatever you choose, as they say in Puerto Rico, “buen provecho!”.

Cap it off with a night paddle or get an early night’s sleep.

If you want one more exciting activity to cap off your evening, go night kayaking! You can paddle through Condado Lagoon on a clear-bottom kayak with LED lights gently guiding the way.

It will be a unique experience as you observe the lights of San Juan and perhaps a sea creature or two. This will be one of two excellent kayaking adventures you can experience in PR. Find more information online here.

Sleep well and wake rejuvenated for a relaxing day into a magical night — bursting with bioluminescence!

Day 4: Head to Fajardo and the Bioluminescent Bay

Spend the morning in San Juan your way before heading to Fajardo.

Did you want to try a new cafe? Did you see a museum you want to check out while in San Juan? Do you just need some time to relax at your hotel? This would be a great time for any of that!

If you’re heading to Fajardo, there are a few options, all of which involve driving. It’s about an hour’s drive away if you’ve rented a car. Not driving? You can hire a public taxi, Uber, or use a private car service (speak to your hotel to see what they can arrange). Be prepared to spend about $80-100.

There is no public transit from San Juan to Fajardo. If you’re comfortable driving, we recommend renting a car for the entire week in Puerto Rico, or at least from Days 4-7 of this itinerary. This will save you money and hassle in the long run.

Grab lunch at La Casita Blanca.

On your way to Fajardo, stop for lunch. For a quiet and wonderfully authentic dining experience head to Santurce for La Casita Blanca, aka “the little white house”.

The restaurant is full of tropical plants, eclectic artwork, and tchotchkes. But really, you’re here for the food: it is incredible! The skirt steak and accompanying rice are mouth-wateringly flavorful. You have to try the tres leches cake, too! You will be served plantain soup upon arrival and given chichaito, a digestif, at the end of your meal, a really nice touch. It’s a bona fide Puerto Rican experience!

They are open daily for lunch and serve dinner on Fridays and Saturdays only. They also have valet parking, which is convenient for parking in this small residential neighborhood.

Arrive in Fajardo and relax on the beach.

Whenever you are ready to get adventuring, head over to Fajardo to check into your new hotel. From there, you can go out and appreciate some of what this area has to offer!

Fajardo offers a great mix of historical sites and some beautiful beaches. Get your snorkel on or call in your inner beach bum for some relaxing time.

Playa Escondida is a great beach to hit if you want to avoid the crowds. It takes about 30 minutes to walk to Playa Escondida from the trailhead, which is near the Governor’s Beach House. However, this beach is one of the most dangerous swimming spots in Puerto Rico, so it is strictly for exploring or relaxing while taking in the view.

If you are looking to swim, Seven Seas Beach is a great place to snorkel, plus, it does not require a long trek to get to the beach. The waters are calm and the sea life is thriving. Palm trees abound and there are plenty of shady spots to enjoy.

There is a restaurant here that may or may not be open. There are also showers and restrooms. Sometimes you can rent kayaks, SUP paddleboards, and snorkeling gear on the beach here.

To guarantee your gear, head 5 minutes south of Seven Seas Beach by car. You will hit Pirate Snorkeling Shack. There are snorkels, kayaks, and SUP for rent on the beach here.

Either of these beaches will be a nice place to spend the golden hour before you prep for your adventure on the Bioluminescent Bay!

Have a BBQ dinner, island style.

Firstly, you’ll want to get dinner. A trip to PR is not complete without a visit to a BBQ. A lot of the beef consumed in Puerto Rico comes right from the island, so there are many BBQ spots around.

La Estación is the place to go for locally sourced, buttery, delicious steaks in Fajardo. They take American barbecue classics and merge them with Caribbean flavors. Enjoy locally sourced fish, meats, and produce. Their brisket is award-winning, the ceviche is made daily, and vegetarian options are available.

Have an enchanting kayak ride through the bioluminescent waters.

Once you have had your fill, grab your gear for kayaking. You will want to bring a towel and possibly a change of clothes for when you exit the water.

The tour provides bottled water, snacks, life vests, and bug spray. Use only eco-friendly bug spray if you bring your own. This is a protected area, and some of the chemicals in traditional bug spray are extremely harmful to this rare ecosystem, particularly DEET.

Once you’ve geared up, an enchanted evening is upon you as you embark on a bioluminescent bay kayaking tour.

Puerto Rico is one of only 3 places in the world where you can experience the magic of a bioluminescent bay! There are 3 bio bays in PR. You can find them in Vieques, La Parguera, and at Laguna Grande in Fajardo; the latter of which is the most famous and where we’ll be tonight!

You will paddle through mangroves into the bay for 2 hours. You will see the bioluminescence light up the shapes of the fish, and possibly sharks, swimming beneath you. The water sparkles as you splash your paddle. It is otherworldly and awe-inspiring, an experience you will never forget.

Book your kayaking tour online here!

Make sure you get a lot of rest for day 5. You will have to have an early morning the following day in order to make your catamaran ride, which meets at 8:15 AM.

Day 5: Set sail in Fajardo

Grab a quick breakfast at a panaderia.

Puerto Rican bakeries or panaderias are flourishing on the island! This would be a great way to start an early day. One of the best spots in Fajardo is Panaderia Monte Brisas.

Like most Puerto Rican bakeries, you can get sandwiches here, too. There is something for all tastes, savory or sweet. All orders are to-go, so grab your sandwiches or pastries and make your way south to Puerto del Rey Marina.

Have a gorgeous catamaran ride or go scuba diving.

As you have seen on your journey so far, Fajardo is an ocean-centered town. It brings opportunities for water sports of all kinds, plus beach lounging and seaside dining. It is not surprising that a catamaran ride is one of the most popular activities to do in Fajardo!

Your final day in Fajardo will be as dreamy as it gets. Head to Puerto del Rey Marina to hop on a catamaran tour!

You will sail for 45 minutes to a deserted island called Icacos. You will have a couple of hours to explore the beach and swim before lunch is served. Enjoy sandwiches, fresh juices, rum punch, and more!

You will then cruise the Caribbean Sea a little more to anchor over the reef. This is a great time to utilize the slide that is aboard the catamaran!

Swim, snorkel, or chill out before your leisurely sail back to the marina. You should arrive back by 3:30 PM.

Book your catamaran ride in Fajardo here!

After your day of fun in the sun, you may want to head back to your hotel to take a rest and freshen up. A seafood dinner will follow.

If you’re PADI certified, you may prefer to go diving here! You can book a two-tank reef drive departing Fajardo — note the early start time!

Book your two-tank dive here!

Dine on fresh seafood.

Head to the coastline for delicious, Puerto Rican-style seafood! Pescaderia Don Candi will show you how the Puerto Ricans do seafood. In short? They do it well!

You should order the fried red snapper. You will be presented with a whole fish, fins and all. The fins are crunchy and yummy so don’t leave them out! They will come with a PR staple, fried plantain, otherwise known as tostones.

They also serve oysters and delicious coconut shrimp dumplings. Don’t forget your rum cocktail or another PR staple, Medalla beer.

As a side note… you may notice on your travels that there are many folks selling rotisserie chicken and pinchos on the side of the road. Pinchos are essentially BBQ meat on a stick. They are cheap, delicious, and a great snack. Both pinchos and rotisserie barbeques are often wonderfully flavorful and make a great choice if you’re trying to save a bit of money!

Perhaps when you complete your dinner, you will want to check out the Cape San Juan Lighthouse of Fajardo for golden hour. Since we are on the east side of the island, watching the sunset over the ocean is not possible; however, the hues of this extraordinary time of day will still impress and delight you!

Head to Reserva Natural Cabezas de San Juan. This nature park will be a great place to walk around while you breathe in the salt air and connect with some history.

The lighthouse was first lit in 1882 and had a large influence in the Spanish-American War. It now sits on a nature reserve that includes Laguna Grande, the bio bay you explored last night! Plus you can explore mangroves, coral reefs, beaches, and lagoons. There is no better way to end the day.

Day 6: Hop the ferry to Vieques

Before you head to Vieques for the night, take the morning to pack up, get breakfast, and tie up any loose ends on your “to-see” list in Fajardo. Then head to Ceiba to catch the ferry to Vieques.

The ferry has specific hours, but it is not always on time. Check the timetables and plan accordingly. Keep your timeline fluid. Vieques in general will force you to slow down and go with the flow!

Cars are allowed on the ferry, but please do not attempt to take your rental to Vieques. The vessel is carrying supplies and vehicles for residents of Vieques. If everyone were to bring vehicles to the island, it would make it very hard for the residents to go about their business.

Please note: it may be very difficult to get on the ferry to Vieques during holidays and weekends due to crowds. It is easier going back, so flying in and out may be your best bet.

If you fly, head to the Ceiba airport and hop on a flight with Vieques Airlink or Air Flamenco. The round trip flight should cost less than $100. I consider these both sightseeing and transportation because the views as so beautiful! So if the budget allows, flying is a great choice.

Once you arrive on Vieques, be prepared to rent a Jeep, motorbike, or a golf cart to get around. There are also taxi services. Make all of these arrangements ahead of time, as you may not get a taxi or vehicle if you arrive without a reservation.

UTV Rental offers golf carts for rent which can be a fun way to explore, or Vieques Car Rental offers Jeeps and SUVs as well as golf carts.

One great way to get acquainted with Vieques is to take a drive around the island! If you rent that Jeep, you are in great shape, as you can drive on dirt roads through the jungle that wind into ocean views. If you are not renting a vehicle, renting bikes is another great option.

The island is mostly reserve land that you have the privilege to explore. They have quite a few roads running through the reserve, and there are hikes to jump on along the way. Be careful if driving as there are wild horses in many parts of the island!

Head towards Sun Bay.

Take your vehicle down towards Esperanza to check out the beach at Sun Bay. You may see wild horses here!

As a side note… the proximity of Playa Sun Bay to the bioluminescent bay makes this a cool beach to peep at night. You may see the dinoflagellates (the creatures that glow) in the surf or on the beach. Can you say sparkle beach, anyone?!

Walk west down the beach at Sun Bay towards Esperanza to enjoy painkillers and a meal at Lazy Jack’s Restaurant and Hostel. Painkillers are a yummy cream of coconut and rum cocktail topped with fresh nutmeg.

Enjoy the lively atmosphere of this Vieques favorite. It is also a great place to stay for the night!

Day 7: Explore Vieques some more and head back to San Juan

The island has two main areas where there are hotels and restaurants: down south at Esperanza or north at Isabel Segunda, near the ferry terminal.

Up north, the best breakfast place is Rising Roost – delicioso! Cafe Del Mar down south is great, too. Enjoy a great breakfast with their house-made bread.

Explore the black sand beach.

After you hit a breakfast spot of your choice, you should head over to Black Sands Beach (Playa Negra). You can walk on the beach from Esperanza if you like. Walk west to reach Playa Negra.

It is inspiring to see the volcanic black sand for yourself! Amp up the magic of your experience and opt for a horseback riding tour on the black sand – contact Esperanza Riding Company for details.

Have a final meal in Vieques.

For a final restaurant recommendation, we have the best for last!

Head to Finca Conciencia for a healthy, ethical, locally sourced meal. Their grouper stuffed with lobster and grilled over mesquite in banana leaves will change your life!

The menu is subject to change but that is the beauty of eating locally. There is variety and change just as the seasons change. When you visit, you will see their sustainable farming practices in action.

It is a sweet place that honors the sacredness of Mother Earth. They are true stewards of the land here. Plus, you may get to sample local honey from their apiaries. Call or email to reserve a spot. See their website for precise directions to their land, as it will not come up on Google.

Take a hike.

Up north, Playa Grande Sugar Mill Ruins is another great spot for a hike.

Hike amongst the ruins and along the coastline. End with a fabulous view of Punta Mulas Lighthouse. This is also a lovely spot for sunset if you end up with time before heading back to San Juan.

Enjoy your final moments in Vieques.

Spend the afternoon relaxing or preparing to head back to San Juan. Your timeline will depend on if you choose to take the ferry back or fly.

If you have time, check out some more beaches, restaurants, or shops. This is a small island with a population of about 10,000. Jobs are limited, so your shopping in Vieques will significantly impact the people that live there in a positive way, especially if you buy hand-crafted products from local artisans. Either way, enjoy the rest of the day your way. It is your last day in Puerto Rico, after all!

You will end your journey back in San Juan. If you drove a rental car to Fajardo, you’ll want to return to Fajardo by bus or by plane and then drive back to San Juan Airport. If you took a taxi to Fajardo, you can save time by flying from Vieques to San Juan.

So ends your week in Puerto Rico. Perhaps you will be going home, perhaps it is on to another adventure!

Hopefully, you feel revitalized from your time on this magnificent island. You will certainly have eaten extremely well if you followed our tips!

From natural waterslides and sailing on the Caribbean sea to kayaking amongst bioluminescence, the adventures you will experience on this Puerto Rico itinerary will surely live in your memory forever.

Puerto Rico is a place that deserves a lot of love, and the people will welcome you so well, you may never want to leave!

It is also a place that has seen a lot of hardships, especially since Hurricane Maria and the subsequent federal failure to address the damages the hurricane caused. As a result, infrastructure is lacking in many parts of Puerto Rico.

The poverty and inequality that pre-dated Hurricane Maria was exacerbated by the impacts of the storm, as well as tourism dollars shrinking during the Covid-19 pandemic. Once the pandemic is over, your visit here will impact the economy of Puerto Rico positively (as if you needed more reasons to come to this awesome place!).

Come to Puerto Rico. Show them some love, and see why they say Puerto Rico se levanta. Puerto Rico will rise again.