San Juan Gay Vacation Guide

San Juan Gay Vacation Guide – Romantic Weekend in San Juan, PR

Planning a romantic LGBTQ getaway to the Caribbean's most gay-friendly island and wedding destination

For couples wishing to marry or honeymoon in a tropical paradise that feels culturally distinct from the United States but doesn’t require passports or currency exchange, Puerto Rico fits the bill perfectly. The bustling 500-year-old capital, San Juan, offers a welcoming LGBTQ scene, alluring beach resorts, and charming Old San Juan, a hilly warren of cobblestone lanes and colorfully painted buildings, many housing noteworthy restaurants and shops.

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Old San Juan is perfect for strolling without a map or a plan—treasures abound in every direction. Stop by 16th-century fortresses, Castillo San Felipe del Morro and Castillo de San Cristóbal, now national parks, and the outstanding Museo de Arte e Historia de San Juan, a fascinating museum set in a Spanish Colonial former market hall. Dine at sophisticated Marmalade, which serves supremely delicious French-inspired Caribbean delicacies, or casual El Jibarito for authentic Puerto Rican fare, including cod croquettes and pork cubes in plaintain gravy. Hipsters, gays, and cocktail aficionados are among the congregants at La Factoría, set in a shabbily grand old building and offering live music and dancing.

Nearby Condado flanks the city’s north shore and contains several posh resorts— it’s also home to a popular gay beach (at the end of Calle Vendig). For a romantic meal of exceptional Puerto Rican food, such as seafood-stuffed mofongo and pork ribs with guava barbecue sauce, book a table at cozy and refined Casita Miramar. San Juan has the best LGBTQ nightlife in the Caribbean—mainstays include Circo and Temptation.

For a taste of the island’s spectacular natural scenery, venture 30 miles east to El Yunque, a 28,500-acre rainforest laced with trails, many leading to rushing waterfalls. Stop for lunch at the colorful kioscos at gorgeous Luquillo BeachCeviche Hut is a standout for first-rate Peruvian fare.

San Juan Gay Vacation Guide
Old San Juan, from Castillo de San Cristóbal. By Andrew Collins


In Old San Juan, 58-room Hotel El Convento occupies a 17th-century monastery, exudes old-world charm, and is lovely for weddings. A small roof-deck and pool afford sweeping views of San Juan Bay. For sheer luxury, it’s hard to beat the century-old Condado Vanderbilt, whose palatial suites have 24-hour butler service and balconies with dazzling views. Amenities include the swanky Vanderbilt Spa and the acclaimed 1919 Restaurant. Next-door, La Concha Renaissance Resort stands out for its festive midcentury-modern vibe. Laze on the beach or by the multilevel infinity pool, and note the myriad wedding spaces, including a 12th-floor rooftop terrace. Also highly inviting and featuring its own secluded lagoon for snorkeling and kayaking, the Condado Plaza Hilton has nearly 600 rooms and a stellar restaurant, Pikayo, helmed by celeb chef Wilo Benet.

Featured image courtesy El Convento