Gay Key West

Gay Key West might be small - it stretches just four miles - but it’s a massive hot-spot for the gay and lesbian traveler. The turquoise water surrounding Key West is full of possibilities. Hundreds of dive and snorkel sites are just offshore. Try one of the gay/lesbian or clothing-optional excursions. Or spend the day battling denizens of the deep aboard a deep sea charter boat. Of course, should you prefer a chaise lounge over a fighting chair, gay and lesbian sunset cruises offer spectacular views of pastel skies as the pulse of Mallory Square festivities beat in the not too distant background. It is almost as if Key West was designed for gay travelers. Our gay and lesbian travel guide keeps tabs on the best so you won’t miss out.

Once home to Ernest Hemingway and Tennessee Williams, the island is a melting pot of diversity, where Bohemians and beatniks intertwine with old money and drones of cruise-ship tourists. Although it’s known for its party lifestyle - if you drink from morning ‘til night, no one will bat an eye - Key West also boasts a rich history of pirating and shipwrecks, and it is a fantastic place to go snorkeling.

Rent a bike for the day and experience Key West off the beaten path. Check out the pastel-colored row houses and all the nooks and crannies of this eclectic island town. Don’t forget: sunsets are free; head to Mallory Square for the daily sunset celebration. In addition to the postcard-perfect sunset, you will be entertained by all kinds of interesting characters. Other island tourist spots include the southernmost point of the United States, the Key West Cemetery and the Ernest Hemingway Home, where the literary icon wrote For Whom the Bell Tolls. (About 60 descendants of Hemingway’s cats roam the property.)

Visit in June for PrideFest, Gay Key West’s annual, weeklong LGBT pride event, or in September for WomenFest, one of the biggest lesbian events in the country. In October, the island celebrates FantasyFest, Key West’s largest annual event, a 10-day Halloween festival that brings an eclectic cast of characters to the island in true Mardi Gras fashion. More than 50,000 revelers flock to Duval Street for the Saturday night parade, which certainly isn’t PG.

NEARBY CITIES:

Islamorada

Located about 90 minutes north of Key West and south of Miami (both among the most gay-friendly destinations in the United States), Islamorada is a must-see destination for all gay and lesbian travelers looking for some fun in the sun. Well-known as a fishing destination, Islamorada is a village with a laid-back and relaxed atmosphere.  Here you’ll find commercial amenities tucked away in tropical landscapes and surrounded by the clear, clean water of the Florida Keys.

While not a traditional gay destination like neighboring cities Miami and Key West, Islamorada offers a variety of gay-friendly hotels, bars and clubs.  Thanks to its very open and accepting population, gays and lesbians are warmly welcomed into most venues in town.