Celebrating its 38th year of delighting audiences, Key West’s Headdress Ball is set for Saturday, Feb. 26, at the Coffee Butler Amphitheater. The glamorous LGBTQ gala typically features about 25 contestants showcasing huge and elaborate original masks, cowls, bonnets and other headgear — with top Florida Keys talents staging dazzling entertainment between headdress presentations.
Teams from around the world will compete in adrenaline-packed sporting events in Key West Jan. 24-31, during the 30th annual Kelly McGillis Classic International Women’s & Girls’ Flag Football Championship. The fun includes acting workshops and performances guided by Kelly McGillis herself, a former Key West resident who co-starred in “Top Gun.”
Although the southernmost island in the continental United States has never experienced a traditional white Christmas, visitors can immerse themselves in seasonal spirit and celebrations throughout December. From tours of historic lighted inns and neighborhoods, to a boat parade featuring dozens of decorated vessels, they’re sure to put the holiday spirit into overdrive.
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.