Curator’s statement
This island is an incredible place to explore, and while you can certainly visit for a couple of days of beach and sun, I think you really need about a week to scratch the surface of the variety of things to see and do in Puerto Rico. We were lucky enough to visit with friends who grew up there and gave us the insider tips for visiting PR. Let me kick you off on planning a trip with this detailed, day-by-day guide to hitting the road and exploring San Juan and Vieques.
The Fora Difference
Book with Diana to access exclusive perks and experiences on your trip.
Killer perks
Free upgrades, spa credits and more—we got you
Personalized recs
Customized travel planning for your style
Insider knowledge
Expert advice from people who’ve actually been there
Where to stay
Unlock perks by contacting Diana to book your trip.
Day 1: Arrive in Puerto Rico
Depending on where you’re traveling from, you’ll likely arrive mid-afternoon or early evening. If you touch down before sundown, we recommend a walk along Bulevar del Valle after you settle in at your hotel — it will give you a great view of the old city walls, cemetery and the citadel El Morro.
Head to dinner at La Garita — the neighborhood is safe during the day but can get a little rough after dark, so we don’t recommend hanging around afterward, but the sunset views are the best in town. They have a variety of mofongos (plantain mash) and margaritas to enjoy!
Afterwards, check out the bar scene. We love the James Beard-nominated La Factoria, the raucous dive bar El Batey and Scryer Rum distillery.
Day 2: Explore Old San Juan
Begin your day with an espresso and a guava pastelito, then take a walking tour to learn the history of the island and the colonial impacts of Spain and the United States. We recommend exploring the US Customs House, Paseo de la Princesa, walking the Paseo del Morro by the Convent and the old gate of San Juan. End with a visit to San Juan National Historic Site.
Puerto Rico has an incredible cultural history — a vibrant contemporary arts scene, religious artifacts from the Spanish colonial days and skilled craftsmen. Explore the many facets of Puerto Rican culture at the Museo de Arte de Puerto Rico, a short car ride away to Santurce neighborhood. Wander the botanical gardens during your visit!
Back in old town, the patio at Princesa is gorgeous, and there’s often live music. It can get busy for dinner when there are cruise ships in port, so we recommend making a reservation.
Day 3: Beach Time
We’ve put it off long enough — it’s time to go to the beach! But first, if you’ve been staying in Old San Juan, it’s time to pack up and move hotels to Condado and pick up your rental car.
Now that you’ve taken care of business — you have many beach options!
Balneario del Escambrón - A very kid-friendly, protected beach with gentle waves, good snorkeling, and a lot of shade.
Condado Beach — You can walk right out of the back door of your hotel, with plenty of beach chairs and amenity options.
La Pared — Just under an hour east of Condado, in the town of Luquillo, you can find stronger waves for a more active beach day.
There are boogie board and surfboard rentals available at Surfing Puerto Rico. The Luquillo beach on the other side of the peninsula also has plenty of sand and a more remote vibe than Escambron or Condado.
Day 4: Spend the Day at El Yunque National Forest
Are you ready to visit the only tropical rainforest in the US national park system? Well, set your alarm clock — in order to preserve the trails and tranquility of the park, El Yunque National Forest only allows a certain number of visitors to access the trails each day. On busy days (again — this surges when cruise ships are in port), they recommend arriving by about 8am.
It’s about an hour drive - on your way out of Condado, make an early morning stop by the Panadería España and fill your belly with as many baked goods as you can handle.
Before you go, download an offline map because reception is limited inside the forest. It IS a rainforest, so make sure you’re ready to get wet — consider your footwear, and think about tucking a jacket or lightweight poncho into your bag for hikes… or at least bring a change of socks! At the park, there are many trails that lead to natural pools — a great one is La Coca, which begins by a waterfall. El Toro trail will take you to a peak within a cloud forest.
Day 5: Coffee Farm and Rum Tasting
Start your day by grabbing a cup of coffee at the source - drive about 30 minutes south of Condado to a small coffee hacienda, Hacienda Muñoz. They offer tours of their working coffee farm, but it’s not required and you can simply purchase and taste their award-winning coffee.
From the hacienda, you’re already halfway to the pernil (pork) highway in Guavate, a windy stretch of road that features several roadside restaurants with succulent, spit-roasted pork. (Like many stateside BBQ restaurants, they have veg-friendly sides, but the overall meat-centric vibe may be a turnoff for vegetarians.) Many people do a bit of a pub-crawl through the area — the open businesses will vary depending on the day, but a few favorites are:
Lechonera El Rancho Original
Lechonera El Mojito
La Placita de Guavate
Close out your day of culinary delights with a private tour and rum tasting at Ron del Barrilito, who have been making rum following traditional methods since 1880. You will be able to taste (or purchase) aged rums that are not available on the mainland, and in addition to a tasting, each tour comes with a craft cocktail at the onsite bar.
Day 6: Visit the Island of Vieques
Today you’ll take a prop plane to the small, rustic-but-beautiful island of Vieques! You’ll be flying out of Isla Grande Airport (SIG), a smaller regional airport where you have two options to get to Vieques — Vieques Air Link or Air Flamenco.
There is a very small local population on the island, and the roads aren’t great, so you’ll certainly want to rent a vehicle and one that can handle potholes — it doesn’t need to be a 4WD, but definitely an SUV and not a car.
Pick up a few beers, some snacks or a sandwich, and head to the beach — that is why you are here! You have MANY breathtaking options:
Playa Sun Bay - There is a cafe near the beach and restrooms/showers, so don’t have to rough it. If you have seen photos of tourists on swings by the beach, here, they’re from this beach.
Playa Negra is quite different, with black sand and dramatic cliffs.
Playa Chiva, while the furthest beach on the island, is known as one of the most beautiful beaches in the Caribbean. It’s great for snorkeling, and there are also restrooms here.
Mosquito Pier is an incredible place to watch a sunset. Get there a bit early and wade out into the ocean from the further end — you’ll find more ocean life (including starfish!) to explore here than entering directly from the beaches.
Treat yourself to fine dining tonight. Visit Placita, located at El Blok or El Quenepo.
Day 7: Beach Day and Mosquito Bay
Plan to spend another day on the beach. Either return to your new favorite spot or try another from the list above! If you feel like being more active, try renting a jet ski at Fun Brothers.
The biobay tours all leave pretty late to ensure that it’s dark enough to see the glow. Before you go, we recommend a quick dinner at Duffy’s, where you can find fun cocktails and reasonably priced fresh grilled lobster.
Afterwards, join a tour group who will take you out to experience the bioluminescent Mosquito Bay in a glass-bottom kayak! If this isn’t something you have seen before, we highly recommend it. It is amazing and certainly bucket-list worthy, as there are only a few places in the world where the conditions are just right for these glowing plankton to thrive.
Day 8: Return Home
You can plan to return to the States on the same day you return from Vieques — we did — but just make sure you pay your time in between when your flight returns to Isla Grande airport (SIG) and when you need to depart from the main airport (SJU) by at least three hours. The two airports are quite close, but traffic can be bad during rush hours and with such a small airline, any delay could cause problems.
Travel Advisor
Diana Turner
Get in touch with Diana
Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.
You can normally expect a response from Diana within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).
This itinerary is part of our ongoing series on travel to Puerto Rico. Looking for more travel inspiration? Check out my guide, Guide to a Long Weekend in Calgary.