Great Escape: San Juan, Puerto Rico

It’s about time Puerto Rico deserves some love, especially from LGBTQ travelers, when its largest city hosts two large Pride festivals.

Words by Marc Graser
Photos by Chase Baker, Akshay Vishwakar, Luis Santiago, Javier Amador and Ramiro Collazo


There’s a saying in Puerto Rico: To Live Boricua means to follow your heart wherever it leads you and find freedom around every corner. 

Puerto Rico has long been a gay-friendly Caribbean island and one of the most accepting destinations, with same-sex marriage legal since 2015, for its more than 3 million residents.

It’s about time Puerto Rico deserves some love, especially from LGBTQ travelers, when its largest city, San Juan, celebrates the community with two large Pride parades and festivals during the first two weeks of June. 

The parties start with San Juan Pride, which fill the bars along Calle Condado and beach clubs at Condado Beach. 

Following is the Cabo Rojo Pride festival, hosted by a sleepy coastal town with 18 pristine white-sand beaches nearby. 

You’ll pretty much be accepted everywhere, but San Juan has three LGBTQ-friendly neighborhoods that are at once foreign yet familiar: Condado, Santurce, and Ocean Park, trendy upscale neighborhoods of hotels, bars and restaurants. 

Puerto Rico has long been a gay-friendly Caribbean island and one of the most accepting destinations, with same-sex marriage legal since 2015, for its more than 3 million residents.

Here you’ll find La Casita Blanca, or “The Little White House,” with an authentic menu and elevated dining room that local influencers flock to. If you order anything local, make sure to try mofongo, Puerto Rico’s popular mashed mix of garlic seasoned fried green plantains filled with vegetables or meat.

San Juan is compact, so you can explore much of the city in a few days. Plan to stay in one of the most popular neighborhoods, each with a distinct vibe: Condado, which is central; Old San Juan, with 500 years of history and colorful Spanish colonial architecture; or Santurce, a grittier hub for vibrant street art, James Beard-nominated restaurants and colorful nightlife. 

The Eleanor Roosevelt district is especially popular with San Juan’s many university students, who gravitate to bars like El Cojo, A Pedir De Boca, and La Esquina de Polo.

There are two gay beaches in San Juan: The popular Atlantic Beach, in Condado, and Ocean Park Beach, in Santurce.

For day trips, consider the mostly secluded Vieques island, off the eastern coast, a nature preserve where you can take boat tours of Bioluminescent Bay (or Mosquito Bay), with microorganisms giving its water a blue-green glow.

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