Ultimate 48-Hour Guide to San Juan, Puerto Rico

1. Introduction

When you’re craving a quick tropical getaway in the US that boasts beautiful beaches, plenty of nightlife options, and adventure activities to boot, Puerto Rico’s capital of San Juan fits the bill. It’s a convenient destination since airlines such as American Airlines, Delta, United, and JetBlue all fly from most major US cities direct to San Juan; and American citizens don’t need a passport because it’s a US territory. Here is where to stay, eat, and go on this romantic Caribbean island.

2. Friday Afternoon: Spa & Dine

Outside the historic district of Old San Juan and connected by a small bridge is the beach and resort area of Condado. Once known as the “Riviera of the Caribbean,” Condado was a popular winter retreat for the rich and famous in the 1920s. Today, it’s a swanky neighborhood with upscale resorts, designer shops, and some of the best restaurants on the island.

Spend your two nights in San Juan sleeping first-class style at the Condado Vanderbilt, which recently underwent a $200 million renovation. Designed in Spanish Revival-style architecture, this hotel nestled on the Atlantic coast breathes spaciousness and class. The Condado Vanderbilt has pool and beach butlers for their private beach and pool cabanas; seven dining options; and is the only hotel in the area with an onsite spa. If you feel like a splurge, the Hammam Ritual is sure to ease any muscle aches from traveling.

Explore Old San Juan

After checking in to the hotel and hitting the spa, get a cab (or an Uber, which has only recently become available on the island) and spend the evening strolling around historic Old San Juan’s cobblestone streets. Tucked among the old churches and peaceful plazas are plenty of shops, galleries, and bars. The stone wall built in the 16th century to protect the city still rises above the Atlantic Ocean.

For a romantic dinner that delivers both on ambiance and taste, don’t miss dining at Hotel El Convento’s Patio del Nispero. The ceiling of this open-air restaurant inside this former convent is a century-old nispero fruit tree. Enjoy seafood dishes such as the pan-fried red snapper or Puerto Rico’s traditional mofongo, a mashed mixture of fried green plantains and pork cracklings filled with chicken or shrimp.

3. Saturday: Hike & Road Trip

Grab breakfast to go and rent a Jeep for some road tripping to El Yunque, the only tropical rainforest in the U.S. It’s about a 45-minute drive to the park entrance. Aim to get there early to beat the crowds and give yourself plenty of time to hike to the observation tower at El Yunque Peak for breathtaking views of the lush green forests and brilliant blue ocean.

Take Scenic Drive

After enjoying the views from above, hop back in your Jeep to take the scenic route back to San Juan. Drive along the two-lane Road 187 through Rio Grande and the beachside town of Pinones. Vast stretches of beach adjacent to the gemstone-blue ocean await, perfect for enjoying the sunset.

End your day with a swanky dinner back at the Condado Vanderbilt’s Wine Spectator award-winning 1919 restaurant. With more than 250 wines to choose from, celebrate your day of hiking to the peak with an unobstructed view of the Atlantic.

4. Sunday Morning: Surf & Sun

Start your last morning in San Juan on a healthy note by grabbing breakfast at Tostado, one of the locals’ favorite brunch spots in Condado. Much of the ingredients are locally-sourced and the menu offers vegan and organic options.

Ride the Waves

Before you fly out, make the most of your morning by signing up for surf lessons at the Courtyard by Marriott Isla Verde Beach Resort. The Isla Verde neighborhood boasts a clean, wide beach with gentle waves perfect for learning to surf. Return home with beach hair and the memory of an adventure as treasured souvenirs.