Gay San Juan San Juan City Guide City Guides > Puerto Rico > Gay San Juan San Juan Suzi SiegelThree 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!” Feel like getting away? Take a trip planned just for you, and let us do all the work. Discover Trip Design Hotels Things to do Things to see Food & Drink Shopping Nightlife Trip Design Serafina Beach Hotel, the first new resort to open after Hurricane Maria, is a sleek, swanky testament to the resiliency of the islandThe best hotels in San JuanYou 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. DreamcatcherThank you for reading Mr Hudson.Subscribe to City Guides or log in to continue reading. Subscribe now Log inSpecial SelectionExclusive Mr Hudson offersOut now from gestaltenMr Hudson Explores Browse the Book Explore more The favourite places of Albert ImperatoNew York-based entrepreneur, classical music lover and honoree of the 2018 OUT 100 Albert Imperato talks to Mr Hudson about The Hudson Valley, his love for travel, and some of his favourite places. Read story > The favourite places of Calum EvansThe Gay Passport helps gay travellers make the most of their vacation by showcasing the best gay-friendly hotels, the coolest bast, the hottest clubs and the most Instagrammable beaches. Read story > A great Seattle weekend trip: from whale watching San Juan islands to the best hikes in Olympic National ParkWhether you want to whale-watch in the shallows around the San Juan islands or hike rainforests within Olympic National Park, Seattle weekend getaways will surely exceed your expectations. Read story > Subscribe to our newsletterYou can unsubscribe at any time by clicking the link in the footer of our emails. We use Mailchimp as our marketing platform. By clicking below to subscribe, you acknowledge that your information will be transferred to Mailchimp for processing. Sign up for exclusive insider promotions SIGN UPBe the first to receive exclusive luxury travel offers and special promotions by subscribing to our newsletter.