Relaxing and Adventurous Puerto Rico 5-Day Itinerary

Advisor - Casey Stein
Curated By

Casey Stein

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  • Puerto Rico

  • Adventure Travel

  • Beaches

  • Family Travel

  • Nature Escapes

  • Relaxation

  • Girls Getaway

  • Beach Town

Beach on a partly cloudy day.
Curator’s statement

Escape to the stunning island of Puerto Rico for a blend of relaxation and adventure! An ideal long weekend getaway with friends, family, or solo. It is a must-visit destination with colorful sites, rainforest adventures, and beautiful beaches where you can unwind with a refreshing piña colada in hand.

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Insider knowledge

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Where to stay

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The Royal Sonesta San Juan

Upmarket hotel overlooking Playa de Isla Verde with breezy rooms and suites.

Fairmont El San Juan Hotel

Set on idyllic Isla Verde Beach, the Fairmont El San Juan boasts modern rooms and resort amenities including a casino, nine restaurants, multiple bars and a nightclub.

Fora Perks
  • $100 hotel / resort credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

La Concha Renaissance San Juan Resort

Get a taste of local paradise at La Concha Renaissance San Juan Resort just steps away from the prestigious Condado Beach.

Fora Perks
  • $100 hotel / resort credit.

  • Welcome amenity

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

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Advisor - Casey Stein

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Day 1: San Juan

Aerial pic of the beach.

Upon your arrival in San Juan, head to your hotel and unwind. Treat yourself to a refreshing piña colada at the hotel bar before hitting the beach. Take the day to relax, savoring the ocean breeze.

In the evening, indulge in an exceptional dinner at Vianda. While everything on the menu is outstanding, be sure to try the Bacalao, it was my favorite dish. The creamy coconut broth was unreal!

With an early wake-up call the next day, it's a good idea to retire early and save the partying for later in the trip. If you do want a night cap, consider exploring the lobby bars at the Fairmont El San Juan Hotel, even if you're not staying there. The chandelier bar which is one of a few bars in the hotel, is beautiful with an excellent rum collection. They also have a casino if you want to hit the slots or play blackjack.

Day 2: Yunque National Forest

River flowing between trees and rocks.

Immerse yourself in a day of adventure in the magnificent rainforest. Companies offer a variety of tour options catering to different preferences. Be prepared to get dirty as you hike through the beautiful bamboo-filled landscapes. Experience the thrill of natural waterslides, cliff jumping, and rope swings for the ultimate adventure. Opt for a half-day tour or choose an extended one that includes a visit to the incredible La Grande Bioluminescent Bay at night. The bioluminescent is indescribable and sadly hard to capture on film, but it is an incredible site to see. Although it is a long day I highly recommend doing both.

If you choose to do a half-day tour, head back to your hotel, reward yourself with a cold Medalla Light and relax at the beach or the pool. Then, go to the T-Mobile District for a fun filled evening. For a casual dining experience, try Sazon Cocina Criolla. The beef empanadas were my favorite. If you're in the mood for something more fancy, indulge in a meal at La Central By Mario Pagan. In addition to trying one of their amazing cocktails. You must get the pasta y queso (gouda croquettes) with an amazing guava marmalade, the prime beef tartare and a side of the pegaito a caballo (be warned this is a huge side dish). After dinner, explore the T-Mobile district, offering a variety of entertainment options, from arcades to movie theaters.

Day 3: Walk and Explore Old San Juan

Colorful buildings on a street.

Begin your day in Old San Juan with coffee and a delectable pastry at Don Ruiz, where the must-try item is the mallorcas, a fried sweet bread that you can get with just cheese and add meat as well. This was amazing. Other bakeries along the way also made this, but this spot was the favorite. Explore the historical charm of the area, starting with the first historic site, Castillo San Felipe del Morro. Purchase a ticket for all the historic sites and begin exploring! From there you can walk back through town, stopping at other sites along the way and ending your site seeing at Castillo San Cristobal. Be sure to stop to take pictures in front of all the murals and colorful homes.

While exploring Old San Juan be sure to indulge in a world-famous piña colada at Barrachina, you can also stay for lunch and try some traditional mofongo. Old San Juan offers a plethora of options from site seeing, galleries, pastries, drinks, and food. Plan to spend the day.

For dinner, I recommend staying in Old San Juan and heading to Deaventura, a traditional spot where the menu is displayed only on a board when you enter. Ask for the sampler platter, customized based on your party's size.

Definitely end your night in Old San Juan for an unforgettable experience at La Factoria. With multiple rooms, each offering a unique drink menu and different ambiance, you can enjoy what feels like multiple nights in one. The cocktails are exceptional, and one room offers live music some nights and everyone is dancing along. You're sure to have the time of your life!

Day 4: Boat Day to Culebra Island with Snorkeling

A green island in sea with clear blue water.

Embark on a catamaran boat ride along the breathtaking white sand shores of Culebra Island, surrounded by clear turquoise blue waters. Upon arrival, snorkel in the pristine ocean, relax on the shoreline, and depending on the tour you choose, enjoy provided drinks and lunch. Your destination will include a visit to one of the island's stunning beaches, which are determined by the tides. This boat day is a must!

After your day of fun, enjoy an incredible dinner at Santaella. Be sure to try the quesadilla with goat cheese, it is remarkable.

For a lively night out, head nearby to La Placita de Santurce, where you can hop from bar to bar until you find one that suits your vibe. This scene is definitely more for somebody who likes to party as the bars stay open all night long.

Day 5: Departure from San Juan

Ocean as seen from an arched opening.

Savor your last moments in paradise by unwinding at the beach, soaking in the final hours of sunshine before your flight home. Don't forget to indulge in a few more guava filled pastries and empanadas. Try the ones from Kasalta in the morning, perfect snacks for your beach day.

Alternatively, if you prefer a full brunch or lunch before heading to the airport, make your way to La Casita Blanca.

Need to Know

Looking for more travel inspiration? Check out my guide, Relax in the Caribbean: Aruba.

Advisor - Casey Stein

Travel Advisor

Casey Stein

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This guide is part of our ongoing series on travel to Puerto Rico.