Need a gay getaway? Puerto Rico is serving hot tropical vibes, all year long.
This Caribbean US territory is the perfect weekend getaway, with direct flights from many major cities, a culture that feels familiar and foreign all at the same time, and warm weather 365 days a year—all without even needing a passport.
For a short visit, focus on San Juan, Puerto Rico’s capital and home to the largest queer community on the island. It is also the LGBTQ nightlife center for, arguably, all of the Caribbean.
With almost 300 miles of coastline, you’ll never be far from the sea in Puerto Rico. For the “gay beach” in San Juan, head to the Condado neighborhood, roughly between Calle Vendig and Condado Avenue. When you’re ready for a casual lunch, the outdoor terrace of Wicked Lily overlooks this stretch of sand and is a great spot to inspect the crowd from above. Feeling fruity? The piña colada is the national drink of Puerto Rico and Piñaloka has an outpost near the beach in Condado that serves fresh cocktails inside a pineapple–refreshing for both the body and Instagram feed. To keep the cocktails flowing after your beach day, walk over to Oasis, Condado’s favorite LGBTQ bar.
If you’re searching for a more zen experience, Paddle Yoga Puerto Rico blends stand-up paddle boarding and yoga, while floating on the calm waters of the Laguna del Condado.
The Puerto Rican art scene has also been heating up in San Juan’s Santurce neighborhood. The (usually) yearly festival, Santurce Es Ley, invites internationally recognized artists to create vibrant murals with Puerto Rico’s finest, up and down La Calle Cerra. The result has turned the area’s buildings into colorful canvases celebrated worldwide. For a guided art walk through Santurce’s El Gandul community join The Art Walk PR. You’ll learn about the neighborhood’s history, its artists, and the push to keep the local flavor front and center. Should you want to leave your artistic mark on the island, The Art Walk PR can also arrange immersive experiences with local artists, where you can assist in painting a neighborhood mural.
After your creative day, reward your artistic endeavors with cheap drinks and sidewalk dancing at the lively El Watusi, one of Santurce’s most popular chinchorros (neighborhood dive bar).
The setting sun gives way to sultry nights in San Juan, with LGBTQ-friendly nightlife that spans all neighborhoods. For craft cocktails with extra shots of history and culture, join Spoon’s “Sip & Savor Cocktail Tour” of Old San Juan. You’ll learn how Old San Juan has evolved over the last 500 years as you walk through the colorful streets and into (literally) some of the world’s most renowned bars. Though the locations can change, you’ll likely stop by La Factoría, named among the World’s 50 Best Bars five years in a row; or the queer-owned El Cafetín, with a vibe that welcomes all.
Afterward, head to La Placita de Santurce. A fruit market by day, the open plaza gets packed on weekend nights with locals dancing on the streets and in the various bars and restaurants lining the plaza. This party is for everyone, but should you want the greatest concentration of our community head to Chueca or El Techo Rooftop.
The Santurce neighborhood is also where you’ll find most LGBTQ-specific nightlife spots. Be aware: Puerto Rican parties start late, so take a nap and plan to arrive after midnight. Start your night with drinks at Toxic Night Club. The blacklight-painted walls are trippy, the drinks are strong and the clientele is muy friendly. Once hydrated, SX is a short walk away and the best bet for cheap drinks and the potential for sexy time in their backroom (geared towards men). Can’t stop-won’t stop? Kweens Klub is not only San Juan’s newest “it” spot but also the largest LGBTQ nightclub in the Caribbean. With room for 700 guests, the night starts with drag shows and ends with dancing till dawn, whether on the massive dance floor or outdoor patio.
San Juan has no shortage of hotel options, from historic grand dames like Old San Juan’s El Convento to the spirited clothing-optional gay guesthouse (but welcoming of the entire LGBTQ spectrum) Coqui Del Mar.
For the full tropical island experience, stay at the Caribe Hilton. The first-ever Hilton outside the continental United States has been welcoming visitors since 1949. Today, the resort is sporting a beautiful $150 million restoration, its own secluded beach, two oceanfront pools, multiple dining options, a massive state-of-the-art spa, and 652 guest rooms to offer you…well, pretty much whatever your heart desires.
The Caribe Hilton is also uniquely centered between San Juan’s three most popular neighborhoods: Old San Juan, Condado, and Santurce. From here, you’re a short Uber ride away from all the city’s hotspots. The resort also claims the honor (though not undisputed) of creating the original piña colada, all the way back in 1954, and celebrates that heritage with tastings and reimagined modern versions of the popular cocktail.
Puerto Rico is a blend of cultures that include Spanish, American, African, and Taíno (the area’s indigenous inhabitants). The welcoming of diverse communities is embedded in the island’s DNA and today, this extends to celebrating the queer community. No other Caribbean island has embraced LGBTQ visitors the same way: including LGBTQ travel information on their tourism website, promoting an inclusive environment that embraces us throughout the island, and even hosting the International LGBTQ Travel Association’s (IGLTA) convention in 2023.
Nicknamed the Island of Enchantment, Puerto Rico will captivate you–whether with the swaying palm trees on its beaches or the swaying hips in its salsa clubs. As the capital city and largest home to the island’s LGBTQ community, San Juan will guarantee a hot weekend getaway and dazzle you from morning to night.