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The Best Festivals in Key West!

If you’re looking for an incredible time in Key West, booking your trip so you can enjoy a festival is one of the best ways to do it. With tons of festivals happening year-round , the party never stops. Check out some of our favorite Key West Festivals in 2022 and 2023 and start planning your trip today.

a group of people flying kites on a beach

Florida Keys Island Fest

Now entering its 31st year, Island Fest is an excellent festival put on annually by the Islamorada Chamber of Commerce. Every year tourists flock to Islamorada for the excellent live music, stunning arts and crafts, and — of course — the All-American Road Vintage Cruisers Car Show! Music acts will range from country and rock to blues and reggae. No matter what your musical taste, there is something for everybody on the main stage at Island Fest. Island Fest 2023 will be April 1-2, 2023 and both days will be packed with exciting entertainment and delicious food. Make sure to stick around Sunday the 2nd for the annual Taste of Islamorada Competition where you’ll be able to try the best dishes from local restaurants and vote on your favorites!

a group of people walking down a street holding an umbrella

Key West Pride

What better place to celebrate PRIDE than on a tropical island? Key West is legendary for its laid-back style and its open and accepting atmosphere. The island has been a premier destination for LGBTQ+ tourism since Tennessee Williams and Frank Merlo popularized it as a vacation destination among the gay scene. The Key West Business Guild, the country’s first LGBTQ+ destination marketing organization, has been working tirelessly since the ‘70s to make Key West one of the most appealing gay-friendly destinations in the world. Key West Pride 2023 will be held June 7-11, 2023, make sure to save the date and book your trip early — hotels will fill up fast! Outside of Pride, the Key West Business Guild also runs WomenFest Key West and Tropical Heat, so there are incredible LGBTQ+ festival options year-round.

a group of people standing in front of a crowd

Ernest Hemingway look-alikes kick off the annual “Running of the Bulls” Saturday, July 23, 2016, in Key West, Fla. The whimsical and much safer answer to the event’s namesake in Pamplona, Spain, was staged as a facet of the island city’s annual Hemingway Days festival that ends Sunday, July 24. Hemingway lived and wrote in Key West throughout most of the 1930s. FOR EDITORIAL USE ONLY (Rob O’Neal/Florida Keys News Bureau/HO)

Hemingway Days

Every year around July 18-23, scores of bearded Ernest Hemingway look-alikes and dedicated fans descend upon the Keys to honor the esteemed writer’s legacy. Look forward to lively literary events including poetry contests, short story contests and more! Don’t miss out on the Key West Marlin Tournament, a celebration of Hemingway’s passion for deep-sea angling with $50,000 in cash prizes. If that’s not enough, there are plenty more events celebrating Hemingway’s dedication to a sporting lifestyle including a 5K paddleboard race and a 100-mile bike race from Key Largo to Key West.

a group of colorful flowers

Key West Fantasy Fest

Looking for the best party in Key West? You owe it to yourself to check out Fantasy Fest. This incredible 10-day, adults-only Halloween party will blow your mind. This event has everything the serious party goer needs: Costume contests, body painting, a kinky carnival with interactive BDSM stations, fetish rooms, bondage and more. This party is definitely not for the faint of heart, but if you’re looking to indulge your wild side, there’s no better place than Fantasy Fest Key West. Fantasy Fest 2022 will be held October 21-30, 2022, so make sure to get costumes ready. This year’s theme is cult classic movies and cartoon characters!

Are You Ready to Party Yet?

Diving into the Key West Festival scene is anything but difficult. Options for all kinds of party goers make Key West one of the best places in the world to hit a festival. Whether you’re looking for something a little literary, a festival that truly welcomes everyone, or just the biggest craziest party you can imagine, you can find all that and more in Key West!