Breezy and tropical, the Florida Keys are accessible via 43 different bridges from the mainland. Iconic for its soft pastel architecture, Key West is an island city that also loves its festivals. Annual celebrations range from a kinetic sculpture parade (April/May) to a raucously colorful Fantasy Fest (October). Here’s our ultimate festival line-up so you can time your trip to suit your fancy.
Conch Shell Blowing Contest at the Conch Republic Independence Celebration. Photo Credit: Rob O’Neal, Florida Keys News Bureau
Conch Republic Independence Celebration – April
Also known as the “Conch Republic,” Key West cheekily proclaims that April 23, 1982 was their informal secession day from the U.S. For 2020, the celebration has been rescheduled for Nov. 27 – Dec 6 and they’re calling on all “Patriots, Pirates and Parties” to celebrate their “FUN-dependence.” Come for the conch shell-blowing contest and stay for the self-proclaimed world’s loooooongest parade that spans from the Atlantic Ocean to the Gulf of Mexico.
Kinetic Art Parade. Photo Credit: Rob O’Neal, Florida Keys News Bureau
Papio Kinetic Sculpture and Art Bike Parade – April/May
Florida Keys folk artist, Stanley Papio, was well known for his wildly inventive refurbished metal sculptures. Now an annual parade that’s popular in many cities, local artists and novices create fantastical structures that must be human powered to move down the streets.
Hemingway Lookalike Contest. Photo Credit: Andy Newman, Florida Keys News Bureau
Hemingway Days – July
The famed author called Key West home during the 1930s and the city celebrates his legacy with a five-day fête. There are poetry readings, a marlin tournament (Ernest loved deep-sea angling) and a spirited look-a-like contest. The festival will be back in 2021.
If you miss his eponymous festival, fear not. You can always visit The Ernest Hemingway Home & Museum that also doubles as a home to almost 50 polydactyl (six-toed) cats, many of whom are descendants from his OG cat, Snow White.
Busker Will Soto walks a tightrope at the sunset celebration in Key West. Photo Credit: Bob Krist/Florida Keys News Bureau
Sunset Celebrations – Every night
It’ll be tough to miss this nightly festival that salutes the vibrant setting sun every evening in Mallory Square. Tourists and locals alike love the various street performers, artists and food vendors that mix and mingle to celebrate art, music and nature.
Costumed revelers representing Mozart’s orchestra in the Fantasy Fest Parade. Photo Credit: Carol Tedesco/Florida Keys News Bureau/HO
Fantasy Fest – October
October tends to be a slower season in Key West so in 1979, local business owners decided to spice things up with an extravagant 10-day festival that’s now 60 parties, street fairs, masquerades and counting. Over 75,000 revelers visit every year in this proclaimed “paradise for grown-ups.” Many events also help support important local fundraising efforts such as AIDS Help of Monroe County.
Where to stay: Five boutique Kimpton hotels in Old Town
