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Colorful umbrellas hanging from a building in San Juan, Puerto Rico

Itineraries for Your Trip to San Juan

San Juan locals share their perfect days.
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3 Days in San Juan for First Timers

Curated by Lydia Schrandtwriter, editor, and award-winning photographer.

San Juan is packed with both historic and cultural appeal, and it’s also surrounded by rain 

forest and beach-lined Caribbean islands, making it an excellent base for exploration. Here are our recommendations for how to spend three days in the Puerto Rican capital.


Day 1

Kick off your trip to Puerto Rico with some sightseeing in Old San Juan. Zip around the 500-year-old city on a guided Segway tour, or lace up your walking shoes and hit the cobblestones the old-fashioned way. No matter how you choose to tour, you’ll learn more about the island’s colonial history while visiting some of its most impressive sites, including the forts Castillo San Felipe del Morro and Castillo San Cristobal—together a UNESCO World Heritage Site—San Juan Cathedral, and Paseo de la Princesa. Continue your explorations in the afternoon with a visit to the Museu de las Américas to learn about the indigenous cultures of the area, the Museum of Art of Puerto Rico, or the Bacardi Rum Factory. In the evening, treat your taste buds to a tasting tour of Old San Juan to sample some of the island’s best craft beers, cocktails, and local foods.

Day 2

No visit to Puerto Rico (or the Caribbean, for that matter) would be complete without spending some time in the water. Choose your level of adventure today. Cruise aboard a high-speed catamaran to the island of Culebra for a day of swimming or sunbathing on the white-sand beaches; head to Vieques Island for some of the region’s best snorkeling; catch a wave during a surf lesson at La Pared Beach in nearby Luquillo; learn to scuba dive or Snuba; or charter a boat for a day of deep-sea fishing for blue marlin, dorado, wahoo, sailfish, or tuna. Back on dry land, sign up for an evening salsa lesson before hitting the town for a night of dancing.

Day 3

Puerto Rico holds the distinction of being home to the only tropical rain forest in the United States, El Yunque National Forest. There’s plenty to do within the park, from jungle trekking and ziplining through the canopy to waterfall rappelling or kayaking, depending on your interest. Alternatively, spend the day exploring two of Puerto Rico’s natural wonders in one tour. Start with a waterfall hike in El Yunque, with time for a cooling swim at the base of the waterfall. After lunch, continue your adventure to the mangrove channels of Laguna Grande, one of the island’s bioluminescent bays. Once the sun goes down, grab a paddle and head out onto the water, where tiny, harmless plankton illuminate the water to create an otherworldly scene.

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