Activist and writer Richard Ammon, the man behind the fascinating and invaluable website GlobalGayz.com, possesses an astounding knowledge about world-wide attitudes toward - and legal rights concerning - lesbians and gays. On his site he's explored not just obvious tourist destinations but also a number of socially conservative nations that relatively few Westerners visit - East Timor, Guinea-Bissau, and North Korea, for example.
Recently, Ammon e-mailed me that he's in the process of writing about three dozen new stories on countries and territories in the Caribbean - so far, he's published new pieces on Puerto Rico, Trinidad & Tobago, the U.S. Virgin Island, the British Virgin Islands, Dominica, Saint Kitts & Nevis, Barbados, and Antigua & Barbuda, with more to follow. I'm often surprised, when talking with generally well-traveled friends and colleagues, that people have little sense of gay attitudes in the Caribbean - that homophobia is rampant on many islands, especially those colonized originally by Great Britain. Arguably the most notorious of these is Jamaica, although that nation's newly electeded Prime Minister, Portia Simpson-Miller, has come out strongly in favor of gay rights, a hopeful sign that even in deeply conservative destinations, the times are slowly changing.
Other places, like Puerto Rico and Curacao, have significant gay scenes and are becoming quite popular with GLBT travelers. In his e-mail to me, Ammon encouraged me to spread the word about "NOT recommending homophobic destinations for travel or cruises." This is a stance I'm sympathetic with, and it resonates with many in the gay community. After all, when we travel to anti-gay places, we're economically supporting governments with homophobic laws and policies.
A counter argument that I've actually made myself at times regarding boycott efforts in Utah and, more recently, North Carolina, is that by traveling and interacting with locals in places where homophobia prevails, gays and lesbians can help improve attitudes and encourage positive social, and eventually legal, reforms.
Both these positions have merit, and I ultimately decide whether to visit, and write about, places on an evolving, case-by-case basis. I've flat-out refused to encourage travel to Jamaica in recent years, given that nation's track record of anti-gay violence and homophobic attitudes, but might it be time, or nearly time, to revisit this policy? I'm not quite ready to, in part because I think there are far safer places for gays and lesbians to travel in the Caribbean (as well as in Mexico and Central America), and also because it's still unclear what effect Prime Minister Simpson-Miller's support will have on Jamaica's laws. But it's a situation I'll continue to watch, and reevaluate, over time.
As you plan your own trips and consider which nations you feel comfortable visiting, I encourage you to read up about them on GlobalGayz.com. And in considering the sometimes complicated political implications of whether or not to spend tourist dollars in homophobic nations, I'm appreciative of a point Ammon made in an article he wrote last year about cruise vacations in the Caribbean: "If more LGBT travelers recommended the ship company bring economic pressure to bear on these little nations by threatening to stop sailing to their ports, Holland-American could make a fine contribution to human rights and increase their respectability among the gay community worldwide."
This strikes me as a helpful, nuanced approach - a reminder that whatever choices we make about where we choose to travel, there's always a way, whether with a carrot or a stick, to encourage destinations to improve their civil rights laws.

Great post. Just would like to add that Playa del Carmen in the Mexico Caribbean is a really great gay destination with plenty of things to do. Check it out at http://www.gayplaya-mexico.com.
Thanks for the comment about Playa del Carmen – I totally agree that this is a great destination for GLBT travelers, and in hindsight, I should have included that along with some of the other gay-welcoming parts of the Caribbean. Appreciate the feedback (and also the link to GayPlayaMexico.com)!