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 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.”
Paula Deen’s husband, Michael Groover, looks a lot like Ernest Hemingway. So much, in fact, that he triumphed over 150 other entrants to win the 2018 Sloppy Joe’s Hemingway® Look-Alike Contest, the undisputed highlight of Key West’s annual Hemingway Days festival.
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.
Legendary shipwreck salvor Mel Fisher, who found the wreck of the 1622 Spanish galleon Atocha, was one of Key West's most colorful and inspirational characters. Adventure lovers can celebrate his legacy during Mel Fisher Days, set for July 12-14 in his longtime “home port.”
Divers and snorkelers can explore part of the continental United States’ only living coral barrier reef Saturday, July 7, while rocking to a unique sub-sea concert (!) that promotes reef protection. It's called the Lower Keys Underwater Music Festival, and it’s unlike any other dive or snorkel experience on the planet.
Every day is an adventure in the Florida Keys, where the subtropical climate and scenic natural setting create the perfect backdrop for high-energy activities. Visitors can experience "only in the Keys" watersports and eco-adventures, unparalleled offshore diving, and organized sporting challenges to test skill and endurance — some with a little wackiness thrown in for added enjoyment.
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.
From celebrations of resident artists’ and writers’ legacies to an art festival that recalls the Florida Keys' fascinating railroad history, "only-in-the-Keys" cultural events spotlight the island chain's heritage as a haven for creative spirits — and draw huge numbers of visitors every year.