Unique Key West Festivals You Can't Miss
Key West may be small - but it sure knows how to throw a party. And festivals are some of the best ways to experience Key West’s quirkiness. Whether you’re looking to attend one of the naughtier events at Fantasy Fest drag-queen-galore or are looking for a more family-friendly celebration like the “Bight” Before Christmas holiday extravaganza, Key West’s festivals won’t disappoint.
Experience the top five festivals that Key West has to offer.
#1 Hands Up for the Fantasy Fest [October]
In 1979, the wildest party in the Florida Keys was born. This 10-day celebration attracts thousands of people to Key West every October for a hedonistic warm-up to Halloween. The festival remains the island’s busiest - and naughtiest - days, so be prepared for big crowds, skin-baring costumes, and some rowdy celebrations. Developed initially to draw tourists during the quiet time between summer and Christmas, today, the festival brings more than 100,000 people from all over the world to The Keys.
This event includes Royal coronation balls, street fairs, drag queens contests, and pet masquerade costume contests, all culminating in The Fantasy Fest Parade. Additional popular festival events include a burlesque show, a Western-themed party at Cowboy Bill’s Bar, and “Wharfstock,” a hippie-themed concert.
Fantasy Fest, where the eccentric and the unpredictable meet.
#2 Key West High Heel Shoe Drop [December]
Leave it to Key West to mark the arrival of the New Year by dropping her royal highness from 20 feet up. This is the new favorite New Year's Eve tradition for locals and visitors. Sushi (Gary Marion), the beloved Key West drag queen, is hoisted into the air aboard an eight-foot-long stiletto.
Thousands of people come to watch the annual "red shoe drop" and celebrate the arrival of the New Year's with family and friends on December 31st. Who are you bringing this year?
#3 The Iconic Hemingway Days [July]
Although the titan of literature, Ernest Hemingway, is no longer with us, some people say you can still catch sight of him in his old haunts once a year in July. Hemingway Days are the best time to celebrate Hemingway, and if you don’t get the hype, just listen to some of the wild and scandalous shenanigans that he got up to on the island.
The festival concludes with an epic lookalike competition at Sloppy Joe's bar, which was Hemingway’s favorite hangout spot. Celebrations include short story competitions for writer enthusiasts, fishing tournaments, and a mock Running of the Bulls. This makes July the perfect time of year to explore his legacy on the island and meet other Hemingway aficionados.
#4 Annual Key West Lobsterfest [August]
If you enjoy fresh lobster, you'll love the Florida Keys. And if it’s lobster you seek, August is the season.
Besides marking the beginning of the Lobster Season, Lobsterfest offers a party for you and your tastebuds. It adds lobster excitement to any August vacation, making it a must-see if you love seafood & big parties. Event highlights include exceptional dishes, free concerts, and the summer's biggest party.
#5 Key West Brewfest [September]
Craft Beer at the beach? YES, PLEASE! If you'd rather drink than eat, this multi-day festival hosted by Southernmost Beach Resort is perfect for you. What's on the menu? Beer dinners, happy hours, brunches, pool parties, and of course, over 100 beers to sample.
If you want to dive into the craft beer world, you can't miss the ultimate reunion with beer lovers from all over.
Ready for the Key West Experience?
Are there others you've heard that you feel we left off the list? Let us know!
These festivals have probably got you packing your bags already. But hold your horses. Do you know the best things to do and places to stay while you’re here? If you're a first-time visitor to Key West or looking to live the experience fully, be sure to reach out to us! We can offer everything from activity recommendations to must-see places. We can't wait to see you!