The Key West Headdress Ball, the premier LGBT event of the annual Fantasy Fest extravaganza, is celebrating its 35th year of dazzling audiences. The glamorous gala takes place Thursday, Oct. 26, and will feature about 25 contestants showcasing outrageous original headdresses — including some far taller their wearers.
The Key West Business Guild’s LGBT visitor center will move to new and larger digs in October along with the Guild itself, acclaimed as one of America’s leading gay business associations. The new location at 808 Duval St. lies within Key West’s famed “Pink Triangle,” which includes a cluster of LGBT bars, entertainment clubs and stores.
Each September, thousands of women converge on Key West for Womenfest, one of the largest gatherings of lesbians and their friends in North America. Set for Sept. 6-10 this year, it features dance parties, sports events, pool parties, and top-notch entertainment -- including two comedy shows by the incomparable Tig Notaro.
Key West's dining options range from a vintage trolley pizzeria with a wood-fired brick oven to a lovely eatery on a secluded island with spectacular views of the Gulf of Mexico. The city is well known for its over-the-top fresh seafood and delicious island-influenced cuisine — as well as stellar eateries showcasing cuisines from around the world.
Key West is known for its inclusive “One Human Family” philosophy that all people are created equal, and for its residents’ kindness and respectful nature that help foster a sense of community and comfort. Here, guest blogger Mandy Murray explains why she believes the island is the perfect place for transgender people to visit.
Key West frequently celebrates its historic Cuban connection with events that showcase our cultural ties to the nearby island nation. One such event will be the inaugural LGBT Art & Culture REvolution, set for Sept. 7-13. Key West attendees can enjoy everything from cigar, rum distillery and art gallery tours to Cuban music events and a special Cuba Libre brunch.
Key West's Tropical Heat, set for Aug. 16-20, features pool parties, sunset sails, snorkel and paddleboarding tours, drag shows, some wicked late-night parties, and even a Gay Key West Trolley Tour spotlighting the island's LGBT heritage -- so check out the hotspots and highlights.
What do visitors enjoy most about the Florida Keys & Key West? Discover insightful answers -- including unique architecture, biking around Old Town, and the welcoming LGBT community -- gleaned in a recent “man-by-the-pool” interview.
Every Sunday afternoon, Key West’s La Te Da hosts an event that has become a weekly tradition for visitors and residents who love a good time. It goes by the unlikely name of Tea Dance, and its music and merriment are overseen by beloved local DJ Rude Girl and her cohort Molly Blue.
The finale of the Stoli Key West Cocktail Classic, called North America’s largest annual LGBT bartender competition, features 17 regional bartending champions from the U.S. and Canada plus a rocking lineup of celebrity judges — and it all takes place June 7-11 in Key West.