With its funky charm, quirky characters, end-of-the-road mindset and reputation as a bastion of the bizarre, Key West might seem more like a fictional setting than a real locale. But while the continental United States’ southernmost city is real enough, it definitely proves the old proverb that reality can be stranger than fiction.
“Athletes” in the weird and wonderful Cow Key Channel Bridge Run, the planet's only “zero-k race,” follow a 300-foot course across one of the Florida Keys Overseas Highway’s shortest bridges. Most wear wacky cow- or bull-themed costumes (some paired with tutus!) and the 2019 race is themed Pirates of the “Cowibbean.”
During the Great Conch Republic Drag Race, female impersonators and their “pit crew” transform part of Key West’s Duval Street into an improvised speedway. The quirky challenge features “dragsters” from across the island, sporting their highest heels and glam racing attire, sprinting down the street in an “only in Key West” event.
In 1982, the Florida Keys & Key West seceded from the United States (for a very good reason) and formed the independent Conch Republic. Come to find out, the irreverent and gutsy spirit that inspired the Keys' secession also sparked the founding of a "country" on the other side of the world: the colorful “Republic of Whangamomona.”
According to paranormal expert David Sloan, Key West is one of the most haunted cities in the entire United States. Visitors can discovery the island's “haunting” appeal for themselves by experiencing David's "ghost hunt" walking tour, taking an eerie excursion by trolley, "meeting" a supposedly supernatural doll or even staying in a lovely inn with a spirit guest or two.
All over the Florida Keys, people are constructing costumes for their cats, dogs, parrots, potbellied pigs, rabbits and other domestic species. What’s behind this strange phenomenon? A wacky annual costume competition for critters, known as the Pet Masquerade, that’s a highlight of Key West’s 10-day Fantasy Fest celebration each October.
Thousands of costumed revelers will promenade through Key West's historic Old Town Oct. 26 during the offbeat Masquerade March, a highlight of the annual Fantasy Fest costuming and masking festival. Famed as “the locals’ parade,” the march typically draws spirited bands and merrymakers wearing everything from lavish feathered and sequined creations to quirky ensembles inspired by the festival theme.
The over-the-top Headdress Ball brings unmatched creativity and spectacular entries to the new Key West Amphitheater at Truman Waterfront Park. Featuring high-quality entertainment and glamorous flair, the gala is the leading LGBTQ event during the island’s fabulous Fantasy Fest masking and costuming festival — and it’s a can’t-miss treat.
Paula Deen’s husband, Michael Groover, looks a lot like Ernest Hemingway. So much, in fact, that he triumphed over 150 other entrants to win the 2018 Sloppy Joe’s Hemingway® Look-Alike Contest, the undisputed highlight of Key West’s annual Hemingway Days festival.
Every day is an adventure in the Florida Keys, where the subtropical climate and scenic natural setting create the perfect backdrop for high-energy activities. Visitors can experience "only in the Keys" watersports and eco-adventures, unparalleled offshore diving, and organized sporting challenges to test skill and endurance — some with a little wackiness thrown in for added enjoyment.