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.
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.
Ernest Hemingway lived and wrote in Key West for most of the 1930s, and the annual Hemingway Days celebrates his talent and exuberant lifestyle. Events include poetry readings, a walking tour of Hemingway sites, a museum exhibit, a scholar’s presentation and the first reading of the Lorian Hemingway Short Story competition’s winning entry.
Renowned for its “One Human Family” philosophy of unity and equality, Key West will welcome visitors to its annual Pride festivities Wednesday through Sunday, June 2-6. Presented by the Key West Business Guild, events will showcase the diversity and enticing atmosphere that make the southernmost city a top vacation destination for LGBTQ visitors.
Fans and friends of the Florida Keys’ Conch Republic can celebrate the irreverent “nation’s” 39th birthday with activities including a pirate adventure, traditional shrimp boil, sunset boat parade, “wearable art” fashion show, sailing excursions and a gourmet dinner and absinthe tasting. The Conch Republic Independence Celebration is scheduled Friday through Sunday, April 16-25.
Don’t miss Key West’s eagerly anticipated “Pride Follies,” scheduled May 22 at the Key West Theater. The production's format is similar to an old-fashioned vaudeville-type show, with a wide array of local talent to entertain audiences. Acts are likely to range from vocals to dancing programs — and maybe even a saucy burlesque performance.
On Jan. 22, 1912, when Ruby Whitlock was eight years old, she watched the arrival of the first train that ever traveled down the Florida Keys Over-Sea Railroad tracks from mainland Florida to Key West. The railroad stretched over 100 miles out into open water in a fantastic ribbon of bridges and track.