WITH DOZENS OF ISLANDS and diverse influences from Europe, Africa and the Americas, the Caribbean offers decidedly different experiences that vary by destination. That makes it even more important for LGBTQ travelers to pick the places that are most gay-friendly and offer the most rewarding ways to enjoy the sun, sand and excitement.

In terms of legal protection and rights, the U.S. territories of Puerto Rico and the U.S. Virgin Islands rate among the Caribbean’s most progressive since they operate with the same antidiscrimination regulations and legalized same-sex marriage laws as the mainland United States. Puerto Rico offers the most extensive gay-specific activities, especially in San Juan, where the gay beach section in the Condado neighborhood packs in sun worshipers during the day, and dance clubs like Circo attract night owls to the nearby Santurce area.

Gay Pride in San Juan, Puerto Rico © MARK CHESNUT/LATINFLYER.COM

In addition, a number of upscale hotels in Puerto Rico are members of the International Lesbian and Gay Travel Association, including La Concha Renaissance San Juan Resort, The Condado Plaza Hilton, San Juan Marriott Resort & Stellaris Casino and San Juan Water Beach Club Hotel.

The U.S. Virgin Islands, meanwhile, offer a more laid-back vibe, with IGLTA member hotels including the Renaissance St. Croix Carambola Beach & Spa and Sand Castle on the Beach on St. Croix, as well as Frenchman’s Reef & Morning Star Marriott Beach Resort on St. Thomas.

In recent years, Cuba gained increased attention from LGBTQ travelers in the United States, thanks to relaxed travel restrictions. Considering recent setbacks in U.S. government travel policies, however, organized tour groups are likely the best way to visit the Caribbean’s largest island — at least for Americans. Companies including Out Adventures and Zoom Vacations offer escorted LGBTQ tours of Cuba that focus on history, culture and other elements of Cuban society.

Curaçao is an especially accessible destination for LGBTQ travelers. The Curaçao Tourist Board, in fact, is a member of IGLTA, while the website pinkcuracao.com offers LGBTQ travel tips. Aruba also offers a generally accepting environment. And, like San Juan in Puerto Rico, the Dominican Republic’s capital city of Santo Domingo boasts a vibrant gay nightlife scene. One thing is for sure: You’ll never get bored in the Caribbean.