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The Caribbean is well known for its homophobia but remains the home to a large community of men who have sex with men, some of whom identify as gay, others who identify as bisexual, and still others who accept neither label. Countries such as the Dominican Republic, Curaçao and Trinidad and Tobago are home to standing gay bars and clubs as well as NGOs serving the gay and bisexual populations. Other countries, such as the smaller island-states of the Organisation of Eastern Caribbean States (OECS) have smaller and more underground groups. In recent years, however, there has been increasing mobilisation of men who have sex with men in these territories.

Jamaica by far has earned a reputation for being the most violently homophobic country in the region. Its Dancehall music came in for much scrutiny during an international campaign in which the lyrics of some entertainers who promoted homophobic violence, including murder, was sanctioned. While many in Jamaica denied the claims of the activists throughout the Americas, Europe and the UK that the calls for the killing of gay men were intentional, the publication in 2004 of Human Rights Watch report, “Hated to Death”, laid bare the violent exclusion and extreme vulnerability faced by gay and bisexual men in Jamaica, often with the support of the judicial system, especially the police. Defenders of Jamaica's record point to a broad culture of violence, arguing that gay men are not singled out but are caught up the waves of violence that typify Jamaican life, especially in its capital, Kingston.

The rest of the Caribbean has a much better track record in regards to homophobia, although discrimination is commonplace. Calypso music, traditionally the music of Carnival fun, has also seen its fair share of homophobic music, including a track produced by veteran Trinidadian music producer Alvin Daniel chanting “we don't want no chi-chi man in di fete” and taken up by Barbados super group Square One. The Dutch and French Caribbean are far more tolerant that their Spanish and English counterparts.

The situation for young men who have sex with other men is particularly dangerous because of the pressure to conform to heterosexuality often combined with isolation from family and community.