With turquoise waters, sandy beaches and tropical heat, the Caribbean is an annual must-go destination for many North Americans seeking a winter escape. The short flights make it that much more tempting.
But for those looking for LGBTQ+-welcoming experiences, not all 700 islands, islets or coral outcrops in this corner of the Atlantic Ocean are created equal.
On Forbes’ 2021 listing of the 20 worst places for LGBTQ+ travellers, Jamaica, one of the most popular and relatively inexpensive islands thanks to its all-inclusive resorts, was ranked number six. This ranking, according to the list’s author, is mostly due to the island’s antiquated laws around homosexuality—being convicted for consensual same-sex sexual activity can bring a sentence of up to 10 years in prison and even hard labour. But Jamaica’s harsh laws are not an anomaly in the region. Tropical paradises like Saint Lucia, Grenada, and Saint Vincent and the Grenadines all have prison sentences for homosexuality according to Equaldex’s equality index of world countries. Protections for transgender people are also rare in the Caribbean.
Still, there are several Caribbean islands that are welcoming and accepting, where holding hands or kissing on sandy beaches will garner little or no reaction. Here are four LGBTQ+-friendly Caribbean destinations you should consider visiting this winter.
Puerto Rico
How can the island that gave us sexy singer Ricky Martin, hijo favorito reggaeton star Bad Bunny, EGOT-winning performer Rita Moreno, several RuPaul’s Drag Race contestants and fabulous astrologer Walter Mercado not top this list?
This unincorporated territory of the United States, which has a population of about 3.2 million people, is just a five-hour flight from Toronto. Americans don’t even need a passport to visit. The close ties to the U.S. mean that many of the federal legal protections for LGBTQ2S+ people enshrined on the mainland also apply in Puerto Rico.
The capital city San Juan’s Pride, usually held in late May/early June, is the biggest rainbow-waving festival there, though several other communities across the island host their own Prides, like the four-day Adventura in Vieques in October, and the Orgullo Boquerón and Cataño PRIDE festivals in June. Puerto Rico Queer Filmfest takes place in November.
When you’re not busy partying with the locals, explore the cobblestoned streets of old San Juan, go horseback riding to secluded rivers and waterfalls in El Yunque National Forest, or visit secluded beaches in Vieques. Read our insider’s guide to the best of LGBTQ+ Puerto Rico for more ideas on what to do while on the islands.
Curaçao
Located in the Lesser Antilles in the southern Caribbean Sea, just off the coast of Venezuela, this island is considered one of the most queer-friendly destinations in the region. There are historical reasons for this. Along with the neighbouring islands of Aruba and Bonaire, Curaçao is part of the Caribbean region that was colonized by the Dutch and which benefits from its long ties with the Netherlands, which is known for its liberal attitudes.
(Former British colonies are much more likely to have laws criminalizing homosexuality—it was the British who introduced most of these laws in the 1800s; that’s how Jamaica got its law in 1864.)
This island of just over 440 square kilometres has a population of around 150,000 people—it can be compared to a small city. But it has its own Curaçao Pride Week (usually in the fall, but check the website for details). The nation’s sole gay bar, GAZE Bar & Lounge Curaçao (Kaya A.M. “Shon Toni” Prince 16, Willemstad), hosts dancing and regular drag nights.
Curaçao has a range of LGBTQ+-friendly accommodations, from boutique hotels to beachfront resorts. Once you’ve got a place to stay, find yourself a spot to lie on the white sand of Cas Abao Beach, check out the colourful buildings along Handelskade in the capital, Willemstad or take in the stunning views and crashing waves at Shete Boka National Park.
Neighbouring Aruba also deserves a mention on this list; you can read more about this progressive, queer-friendly destination in our 2024 guide to the island.
Saint Barthélemy
Haven’t heard of this 25-square-kilometre French-speaking island in the Caribbean’s Leeward Islands group? Maybe it’s time to take notice. More commonly known by English-speakers as St. Barts, this destination is popular for its white-sand beaches, luxe vibes, great shopping and exclusive resorts.
While there is no gay scene on the island, there is a general openness to the LGBTQ+ community, thanks in part to the island’s connections to French culture and—more importantly—its legal system and enshrined protections.
A local has created an LGBTQ+ visitors’ guide to the island highlighting where to go, what to do, and the secrets to finding the best parties and events. One key tip: because many visitors rent villas, private pool parties are popular. Another: La Cantina (Rue du Bord de Mer, Gustavia) is a gay-owned bar that is welcoming to everyone. And one last tip: Gay men usually congregate on the left and right sides of Saline Beach, which is also the country’s only clothing-optional beach.
Cuba
Yes, Cuba has been having a tough go of it lately, with the repeated failure of its power grid followed by Hurricane Oscar along the eastern side of the island in late 2024. But this country, and its LGBTQ+ communities, have experienced far worse. (For context, read the late Cuban poet and activist Reinaldo Arenas’ 1992 autobiographical novel, Before Night Falls, which includes his recounting of his departure from Cuba in 1980, when then-president Fidel Castro allowed/encouraged Cubans that Castro saw as undesirable, including LGBTQ+ people, to leave the country en masse.)
Things have changed dramatically since Arenas’s time. In the last couple of decades, the Cuba government has made great strides in recognizing LGBTQ+ rights, including equal marriage, which was legalized in 2022. Attitudes have changed, too. Cuba has emerged as a vibrant destination with an active LGBTQ+ community that includes out artists. For visitors, it’s got everything from nightclubs and bars to queer-focused resorts.
Havana is Cuba at its queerest. Visit the historic sites in Old Havana during the day, or hang out at Mi Cayito Beach, which is known as the city’s gay beach. Then at night visit gay venues like Cabaret Las Vegas, XY Bar and Café Fortuna Joe.
Elsewhere in the country, popular resort areas include Varadero, Cayo Guillermo, Cayo Coco and Santiago de Cuba, all of which have resorts that are LGBTQ+ friendly.
