48 Hours in San Juan, Puerto Rico

View of the ocean from the patio of the Condado Vanderbilt in San Juan, Puerto Rico.
Soak in the view of the ocean from the patio of the Condado Vanderbilt in San Juan, Puerto Rico. Condado Vanderbilt

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.

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Friday Afternoon: Spa & Dine

Inside the Condado Vanderbilt's 1919 restaurant in San Juan, PR
Condado Vanderbilt

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, and again in the 1960s when it went through a revival. Today its 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, thanks in part to the clean white walls, high ceilings, and elegant archways. 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 being on a plane. This traditional Turkish treatment involves lots of steam, laying on a slab of smooth heated marble and a body exfoliation using cleansing black soap.

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 also plenty of shops, galleries, and bars. The stone wall built in the 16th century to protect the city still rises above the Atlantic Ocean. Just outside the city walls, you’ll find the Paseo de la Princesa, a walkway along the water that’s lined with artists, musicians, entertainers, and craft vendors on weekend nights.

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. Opt for seafood dishes such as the pan-fried red snapper with mashed plantain and fresh papaya sauce; or try Puerto Rico’s traditional mofongo, a mashed mixture of fried green plantains and pork cracklings that forms a shell and is usually filled with chicken, skirt steak or shrimp. You might also ask the chef to customize your meal using herbs from their onsite garden.

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Saturday: Hike & Road Trip

View from El Yunque's peak, a rainforest in Puerto Rico.

Grab breakfast to go and rent a Jeep for some road tripping to El Yunque, the only tropical rainforest in the U.S. (There’s a Budget rental across the street from the Condado Vanderbilt and Enterprise is only a few minutes' ​walk away). It’s about a 45-minute drive if you take the main toll highway 66 until it ends at 3 East and you take a right to the park at the third traffic light. 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 a breathtaking view of the lush green forests and brilliant blue ocean before the mist that usually creeps in around noon cloaks the landscape. You can actually drive through the park up to the Las Picachos Trailhead for a shorter climb that still has gorgeous views, or take the longer but more scenic El Yunque Trail for a five-mile, three-to-four-hour roundtrip hike along many different types of forest. Pack a lunch to eat at the peak, but know that there are also a few vendors inside the park selling snacks and drinks.

Take Scenic Drive

After you’ve gotten a view of eastern Puerto Rico from above, hop back in your Jeep to take the scenic route back to San Juan by driving along the two-lane Road 187 through Rio Grande and the Afro-Puerto Rican town of Loiza to the beachside town of Pinones. Vast stretches of beach melt into the gemstone-blue ocean and go on for miles. If you pull off the road, you’ll find tracks running through the sand dunes with parking spots carved out in between the tall grasses and overlooking the waves. Grab a cheap beer or coconut water from one of the many roadside kiosks that also serve up fried snacks made over fires, such as bacalaítos (fried codfish fritters). Enjoy the sunset, but be sure to head back to San Juan before dark as this road isn’t the safest at night.

Contrast a jam-packed day of hiking and sand with a swanky dinner back at the Condado Vanderbilt’s Wine Spectator award-winning 1919 restaurant. With more than 250 wines to choose from, you can toast your accomplishment of hiking to the peak with an unobstructed view of the Atlantic, thanks to floor-to-ceiling windows. A Michelin-starred chef may be preparing you beautifully-presented dishes such as caviar with coconut-cucumber broth.

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Sunday Morning: Surf & Sun

underwater view of a surfboard
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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 takeout containers are compost-friendly. There are vegan and organic options, fresh-squeezed juices, and deliciously smooth lattes. Try the vegan pumpkin coconut pancakes and any of the breads made with organic flour in-house.

Ride the Waves

Make the morning count before you fly out by signing up for surf lessons at the Courtyard by Marriott Isla Verde Beach Resort (about $50 per person per hour). The Isla Verde neighborhood is east of Condado en route to the airport, and, though not as glitzy as Condado, it boasts a clean, wide beach with gentle waves perfect for learning to surf—and one of the best stretches of beach on the island. If not you’re heading back to the hotel, you can rinse the saltwater off in the outdoor showers and change in the resort’s bathrooms. Just be sure to bring a plastic bag to pack your wet bathing suit for the plane. Return home with beach hair and the memory of a fun adventure as vacation souvenirs.