Cuba
Now that the ban on traveling to Cuba has been lifted, the island has become increasingly popular among travelers. Fidel Castro's daughter, Mariela, heads the Cuban National Center for Sex Education and has advocated for LGBT rights. Many of the island's B&Bs (casas particulares) are gay-friendly. But the hottest spots on the island are Vedado, Havana's de facto gay neighborhood, and Mi Cayito the unofficial gay beach.
Curacao
Hosting the week-long South Caribbean Pride Festival in May, Curacao is one of the most gay-friendly islands in the Caribbean. A whopping 17 hotels and attractions holding membership in the IGLTA. Check out Café de Heeren, Bermuda Caribbean Discotheque and Mambo beach club for an evening of dinner, drinks, music and dancing.
Puerto Rico
Trendy neighborhoods like Condado and Sancture make San Juan one of the most gay-friendly destinations in the Caribbean. The Calle Vendig area features a popular gay beach, weekly drag shows and plenty of cafes and restaurants. Check out the Atlantic Beach Hotel and the gay-owned Oceano. Another popular LGBT destination in Puerto Rico is Vieques Island, which features a variety of LGBT-friendly guesthouses.
St. Martin/St. Maarten
If you're looking for a more lavish retreat, St. Martin/St. Maarten is the place to be. Featuring touches of European culture, this two-culture island is known for its French (St. Martin) and Dutch (St. Maarten) influences. Located near Cupecoy Beach, one of St. Maarten's clothing optional gay beaches, is the Rainbow Beach Club, which is the only gay guesthouse on the island. Additionally, Belmond La Samanna and Sonesta Ocean Point (adults only) are both IGLTA members and are very welcoming the LGBT community. For drag entertainment, head to L'Escargot for French cuisine and a fabulous show.
US Virgin Islands
The U.S. Virgin Islands consist of St. Thomas, St. Croix and St. John, which are all accessible to one another by ferry if you're into island hopping. While St. Thomas has a nightlife that caters to the LGBT community, St. Croix is largely considered the “gay mecca” of the U.S. Virgin Islands. In St. Croix travelers can check into the gay guesthouse Sand Castle on the Beach or The Palms at Pelican Cove.