The most gay-friendly Caribbean islands are the U.S. possessions, most notably San Juan, which is hailed as the "gay capital of the Caribbean" and offers gay guesthouses, nightclubs, bars, and dance clubs. To a lesser extent, the U.S. Virgin Islands are welcoming, too.
The French islands -- St. Barts, St. Martin, Guadeloupe, and Martinique -- are technically an extension of mainland France, and the French have always regarded homosexuality with a certain blasé tolerance. However, don't let your guard down: Severe attacks and hate crimes against gay men have been reported.
The Dutch islands of Aruba and Bonaire are quite conservative, so discretion is suggested. But in a surprise move in 2005, their sister island of Curaçao became the first in the Caribbean to announce that it was embracing the gay and lesbian community, urging such travelers to visit the island as a gay-friendly destination, and some hotels have joined the Gay & Lesbian Travel Association. Even certain nightclubs in Willemstad highlight their gay-friendly atmosphere in an attempt to attract patrons from this community of travelers.
Gay life is fairly secretive in many of the sleepy islands of the Caribbean. Some islands even have repressive antihomosexual laws. Homosexuality is actively discouraged in places like the Cayman Islands, but as a result of pressure from gay advocacy groups, past homophobia is slowly giving way to tolerance. In Barbados homosexuality is illegal, and there is often a lack of tolerance in spite of the large number of gay residents and visitors on the island.
Jamaica is the most homophobic island in the Caribbean, with harsh antigay laws, even though there is a large local gay population. The famous all-inclusive Sandals of Jamaica had until 2004 a discriminatory policy of admitting only male-female couples. However, under pressure they were forced to rescind the ban and admit same-sex couples.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.