Fritzie Estimond is a welcoming presence at the Key West Business Guild’s LGBTQ Visitor Center — and the guiding spirit behind the guild’s annual events. What does she like best about Key West? The “small community” feel, the acceptance that allows people to be their authentic selves, and what she cheerfully calls “the weird.”
Each year bicyclists navigate the entire Florida Keys island chain, along scenic Overseas Highway and Heritage Trail routes, during the 165-mile Miami to Key West trek known as the SMART Ride. Now in its 18th year, the event has raised an astounding $12.5 million for AIDS service organizations in Florida and the Keys.
Great news — Fantasy Fest is a go for 2021! Revelers can enjoy over 50 costume contests, masquerades, parties and performances during the high-energy annual event, though traditional large-crowd highlights aren’t taking place to protect against potential coronavirus spread. This year's popular masking and costuming festival entertains partygoers from Oct. 22 through Oct. 31.
Key West is known as one of the most haunted cities in the United States. Visitors can experience several year-round ghost tours that are delightfully unnerving, including an award-winning trolley tour with a “ghost host” and the exploration of a haunted Civil War–era fort where they encounter the eerie Robert the Doll.
Who says the fall season has to be dull and gloomy? Instead, plan an adrenaline-packed vacation in the sunny Florida Keys, and enjoy balmy temps and delightful ocean breezes while indulging in “bucket-list” adventures — like exploring the continental United States’ only living coral barrier reef, sportfishing or even skydiving above the island chain.
Whether shopping for offbeat gifts or fine art, the emporiums of Key West provide a warm welcome for some well-deserved retail therapy. Emporiums range from the pioneering Key West Aloe, Graffitti and In Touch to the Gingerbread Square Gallery, opened in the early 1970s by Richard Heyman, the nation’s first openly gay mayor.
Traveling through the Florida Keys to Key West is a bucket-list adventure in itself. Driving the historic, 127-mile Florida Keys Overseas Highway is considered by many travelers to be the trip of a lifetime. And flying over the island chain and surrounding waters into Key West International Airport is an equally memorable experience.
What are some of the best ways to keep cool on late-summer days, while also enjoying everything Key West has to offer? Consider taking an all-male snorkel and sandbar excursion, lazing at “Fort Liz Taylor Beach,” discovering the story of Key West’s most famous LGBTQ resident, or comfortably chilling at a guesthouse pool.
For scores of women, early September in Key West means enjoying adventures in the Atlantic Ocean and Gulf of Mexico waters, plus entertainment, parties with like-minded people, and relaxation on an accepting subtropical island — all during Womenfest. Highlights include entertainment by Sister Funk and a sunset sail on a 75-foot luxury catamaran.
Tropical Heat offers five days of sizzling happenings in Key West, whose openness and respect for diversity have made it a world-renowned gay vacation destination. Presented by the Key West Business Guild, the festival features intriguing events ranging from pool parties to a sunset cruise to late-night gatherings at LGBTQ bars and nightclubs.