Gay San Juan San Juan City Guide

Three things that rarely go hand-in-hand for gay travellers are top-tier cities with top-shelf beaches that are legit gay-friendly. Well, this rainbow unicorn exists and it’s called San Juan. The capital of Puerto Rico is one of the few cities in the world, and the only one in the Caribbean, that checks all those boxes and then some: the colourful colonial architecture, the cobblestone streets, the picture-perfect beaches, the 16th-century landmarks, the James Beard-awarded restaurants and bars, and the banging gay scene. San Juan is the undisputed queen of LGBTQ+ nightlife in the Caribbean. This place sparks joy, people. The kind that makes you want to yell, “Woo-hoo!” or, as the Puerto Ricans would put it, “¡Wepa!”

Serafina Beach Hotel, the first new resort to open after Hurricane Maria, is a sleek, swanky testament to the resiliency of the island

The best hotels in San Juan

You have to imagine that a hotel built in a monastery adjoining the second-oldest cathedral in the Western Hemisphere is something special and it is. Hotel El Convento in a 350-year-old former Carmelite convent is the gold standard of historic hotels, with its high ceilings, handcrafted tiles, dramatic archways, wooden beams and views of San Juan and the bay from every room. Serafina Beach Hotel holds a special place for Borinqueños because it was the first new resort to open after Hurricane Maria. A sleek, swanky testament to the resiliency of the island, stylish locals flock to the pool on weekends to rent the pricy cabanas, get bottle service going and dance to international DJs. Opulent, modern and historic when it opened in 1919, the Condado Vanderbilt hosted Charles Lindbergh, Bob Hope and FDR as guests back in the day. It recently underwent a massive expansion and modernization and is presidential-worthy again today. If you’re more of the crunchy, meditating, kombucha-drinking type, the Dreamcatcher might be more aligned with your chakras. Small and chic with no TVs (amen), it’s billed as San Juan’s only vegetarian hotel. They offer yoga on the beach that conveniently is just steps away. If architecture is your thing, the Dream Inn PR’s design is striking. The 13-room guest house is built in a tropical modern-minimalist aesthetic that plays off the concrete vernacular style seen all over the city. The whole building is designed to highlight the interchange between light and shadow. The tranquil koi pond and rooftop lap pool are lovely.