The over-the-top Headdress Ball brings unmatched creativity and spectacular entries to the new Key West Amphitheater at Truman Waterfront Park. Featuring high-quality entertainment and glamorous flair, the gala is the leading LGBTQ event during the island’s fabulous Fantasy Fest masking and costuming festival — and it’s a can’t-miss treat.
From an island-style street party to an over-the-top headdress gala, Key West's fall schedule includes so many reasons to plan a southernmost escape. Don't miss the two-day Goombay Festival Oct. 19-20, celebrating Key West’s Bahamian heritage, or the dazzling 36th annual Headdress Ball on Oct. 25 featuring contestants’ flamboyant masks and outrageous headdress regalia.
Key West’s legendary Fantasy Fest is coming up Oct. 19-28 with a roster of world-class festivities. This year's theme is “Oh … The Games We Play!” — and the over-the-top costuming, unparalleled parties and amazing energy generated by the festival will impress even the most seasoned party animals out there (you know who you are!).
Key West's Womenfest, taking place Sept. 5-9, is renowned as one of North America’s largest gatherings of lesbians and their friends. It was created to allow singles, couples and groups of women to experience camaraderie, adventures on land and sea, live entertainment and lively celebrations for “Party Girls.”
The free-spirited island of Key West is famed for its lively celebrations and balmy year-round subtropical weather — but in August the party scene really heats up. The reason for this “Island Fever” is the Tropical Heat festival, which will entertain revelers Wednesday through Sunday, Aug. 15-19, with a sizzling long weekend of all-male adult events.
Key West's sun-drenched days and cool island breezes beckon visitors to get out and explore countless outdoor activities — all sure to excite the senses and rejuvenate the spirit after a long, chilly winter indoors. Discover five "locals' favorite" activities that reveal the quintessential appeal of Key West.
Artists, authors, playwrights and poets have been lured to Key West and seized upon its one-of-a-kind environment of creativity, natural beauty and sometimes eccentric qualities — making it the muse for some of their most acclaimed career accomplishments.
Key West launches its annual Pride celebration with a June 2 theatrical performance aptly named “Pride Follies.” The production’s format is similar to an old-fashioned vaudeville-type show, presenting a wide array of skilled local talents to delight audiences.
Key West will welcome visitors to Pride festivities June 6-10 -- with a lively roster of activities showcasing the diversity and equality that help make the southernmost city a top vacation destination for LGBT visitors from around the world.
Entertaining guests in Key West is a breeze with limitless opportunities to raise the “fun-o-meter” sky-high. One of the top “go-to” places is La Te Da, renowned for its excellent food, decadent libations and lively array of entertainment options.