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.
Attendees at the Key West Food and Wine Festival can enjoy gourmet galas and tastings, art and wine experiences, wine dinners, seminars and activities that spotlight the Florida Keys’ culinary scene and talented chefs. Equally appealing are the glimpses the festival offers into the island chain’s unique heritage, culture and warmly welcoming vibe.
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.”
New Year’s Eve celebrations in Key West typically feature balmy weather and a warmhearted welcome for visitors eager to escape freezing northern temperatures. Festivities include several offbeat takeoffs on the traditional ball drop in New York’s Times Square — even one that stars drag queen Sushi being “dropped” in a supersized red high heel.
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.
The largest shipwreck available for sport diving in the Lower Keys remains a popular stop on the Florida Keys Wreck Trek for divers, and a relatively easy introduction to wreck diving for novices. The 210-foot-long Adolphus Busch, sunk intentionally in 1998, lies between Looe Key and American Shoal, southwest of Big Pine Key.
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.
The bearded brotherhood of Hemingway Look-Alike Contest winners gained a new member July 25 in Key West, home of legendary author Ernest Hemingway for most of the 1930s. Zach Taylor, a 63-year-old white-bearded Georgia man, triumphed over 136 other entrants to win the contest that highlights the island city’s annual Hemingway Days celebration.