Gay San Juan San Juan City Guide

Curation by Yasmina Rodríguez, words by Suzi Siegel

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!”

The best hotels in San Juan

There are hotels, and then there is Hotel El Convento. Nestled within a 17th-century Carmelite convent at the very heart of Old San Juan — a stone’s throw from the second-oldest cathedral in the Western Hemisphere — it is the gold standard of historic luxury in the Caribbean. The 81 individually appointed rooms marry Spanish Colonial character (Andalusian tile floors, exposed mahogany beams, handcrafted furnishings) with genuine modern comfort, many affording sweeping views across San Juan Bay. The rooftop plunge pool and Jacuzzi deliver one of the finest sunset vantage points on the island, whilst the daily Manager’s Reception on La Veranda Terrace — canapés, wine, unhurried conversation — sets the tone for the kind of gracious service that has made El Convento a legend.

If palatial oceanfront grandeur is more your register, the Condado Vanderbilt answers the brief magnificently. Commissioned by Frederick William Vanderbilt and conceived by the architects behind Grand Central Terminal, it opened in 1919 as the island’s first luxury hotel and has since welcomed presidents, aviators and Hollywood royalty. Fully restored, it occupies a prime position in the upmarket Condado neighbourhood — steps from the lagoon and a short stroll from the queer-friendly bars that animate this part of town — with four pools, a full-service spa and the exquisite 1919 Restaurant to keep you thoroughly occupied. For those who prefer their luxury with maximum social voltage, the Fairmont El San Juan Hotel on Isla Verde Beach is the undisputed grande dame: its hand-carved mahogany lobby, crystal chandelier, four pool areas, Well & Being Spa, nightly cabaret at Chico Cabaret and 13 restaurants and bars sprawl across 15 beachfront acres of unapologetic glamour.