Planning a Weekend Trip to San Juan, Puerto Rico

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Advisor - Noah West
Curated By

Noah West

  • San Juan

  • Arts & Culture

  • Beaches

  • Couples Travel

  • Puerto Rico

  • Beach Town

  • Sightseeing

  • History

A wall with painting in San Juan, Puerto Rico.
Curator’s statement

Whether you’re looking for a relaxing beach getaway, an exciting rainforest adventure, an immersion into unique architecture or an opportunity to eat great food on every corner of every street, San Juan has something for everyone. This beautiful and unique Caribbean island is easy to access, simple to navigate and very hard to leave. Since San Juan is one of my wife and my absolute favorite travel destinations, I wanted to share with you the restaurants we’ve fallen in love with, the things that fill our itinerary while we are there and the beautiful places we stay at when we visit our home away from home.

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Where to stay in San Juan, Puerto Rico

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Things to do in San Juan, Puerto Rico

A castle moat.

See the amazing Castillo San Cristobal and Castillo San Felipe del Morro

These two castles are full of rich history and amazing architecture, but that is not all. Castillo San Cristobal offers wonderful views of the brightly colored houses of La Perla, creating one of my favorite picture spots in the city while the lush green park with skies constantly full of kites outside of Castillo El Morro is one of my favorite spots to grab a drink or a snack and people watch for hours.

Adventure in the El Yunque Rainforest

While the El Yunque is a bit of a trek (45 minute drive from San Juan), it is 100% worth it to experience the only tropical rainforest in North America. My wife and I opted for a private tour that included serene hidden jungle pools, cliff jumping, breathtaking views and much more, making it an experience that we will both never forget.

When in Puerto Rico, Save a Gato

Located within Old San Juan alongside the beautiful Paseo del Morro walkway is Save a Gato, a local non-profit dedicated to the welfare of the cats of Old San Juan. Stray cats are nearly everywhere in this neighborhood, but they are heavily concentrated in this area, making for a great place to walk around and see all the cute fur babies. Don’t forget to volunteer with or donate to Save a Gato while you are in the area!

Go Snorkeling at Flamenco Beach

Anywhere I travel, if there’s an opportunity to go snorkeling, I always jump on it. That being said, the white sand and crystal clear waters of Flamenco Beach are a must see when visiting Puerto Rico. I definitely recommend booking a fully inclusive snorkeling tour from San Juan to Flamenco Beach on the island of Culebra.

Walk the Caleta de Las Monjas

If I had to pick one place to be out of all of San Juan, it’s right here on this street. The cobblestone road lined with colorful walls, intricate doors and bright, blooming flowers makes for the most picturesque place to take in a Puerto Rican sunset with a gelato or pina colada in hand.

Take in the Beautiful Doors of San Juan

Everyone with google on their phone can find an article suggesting that they should go take a picture in front of the famous Puerto Rican flag door in Old San Juan, which I have no arguments against, but nearly every door in this neighborhood is a marvel. Each door has its own personality and history that continues to tell stories to everyone who walks by it.

Have a Photo Shoot on Umbrella Street

One of the most iconic photos that San Juan has to offer is standing under the colorful umbrellas that span the sky. A must stop for those who want to keep their Insta feed on point. Kick Back with a Drink in Hand at the Pool or Beach. Whether you’re on the rooftop of Hotel El Convento or the beach in front of the Condado Vanderbilt Hotel, there are ample opportunities to take in the hot San Juan sun with your toes in the water and a Piña Colada in hand.

Places to eat & drink in San Juan, Puerto Rico

Empanadas in Puerto Rico.

Ajo Del Pais: When you’re walking through Old San Juan in the peak of summertime heat and you need a reprieve from the sun, you step into Ajo Del Pais. That is precisely what happened on my first trip to San Juan and I’m so thankful I stepped inside. Ajo Del Pais is a laid back eatery with a large menu and great drinks. I recommend creating your own “tasting menu” of Puerto Rican specialties by ordering several of the small plates.

Chocobar Cortes: Attention all chocolate lovers, put Chocobar Cortes on your itineraries now! Stop by for a menu of chocolate drinks, desserts, cocktails and several other offerings like the chocolate grilled cheese and chocolate baby back ribs.

Stuffed Avocado: Think Chipotle, but instead of a flour tortilla, you’re building your bowl into (or more onto really) an avocado. Quick, casual and a great place for some unique and tasty bites.

La Lanterna: This Italian restaurant is an absolute gem. Hands down my favorite dining experience in San Juan. Great location, beautiful atmosphere and incredible food. It’s hard for me to put into words how much I love eating here.

Anita - La Mamma Del Gelato: A big piece of advice I’d offer regarding Anita is to go here early in your trip! That way, if you fall in love like I did, you can go back as many times as possible for more and more Gelato before you have to go home.

La Marqueta Food Hall: Located on the beach in Condado, this food hall is home to a huge variety of trendy and tasty restaurant offerings, and you may even stumble on a party hosted by Diplo if you’re lucky. They are only open on Thursday-Sunday, so plan accordingly, and be sure to check their events calendar ahead of time as they have entertainment events going on all the time.

Sage Steak Loft: If you have an occasion to splurge on dinner, I recommend you do it at Sage Steak Loft within the O:live Hotel. The menu and food are great, drinks are even better, but the view of the lagoon from the rooftop dining area is what makes this place so special. You (or me, as your travel advisor) definitely need to call ahead to ensure you can get one of the few tables with access to this amazing view.

La Factoria: Ranked #24 on North America’s 50 Best Bars List and voted as the best bar in the Caribbean, La Factoria is my favorite place in San Juan to get a drink. The vibes are great and drinks even better.

Need to Know

For more travel tips, check out Fora Advisor Lona Cosmas’s guide, Solo Vacationing & Exploring San Juan, Puerto Rico.

Advisor - Noah West

Travel Advisor

Noah West

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This guide is part of our ongoing series on travel to San Juan.