Events
It's not just another day in paradise! You'll find doings and happenings up and down the Keys, nearly every day of the year. Check out the latest fun and frolic below.
Only-In-The-Keys Festivals & Events
There’s always something happening in the Florida Keys & Key West, from eclectic festivals focusing on the area’s colorful history, arts and notable cuisine to events that celebrate the Keys’ unique environment, underwater adventures and quirky ambiance.
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Key West
Mile 0 Fest
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Experience Mile 0 Fest in the stunning Florida Keys! Enjoy five days of top Texas Red Dirt & Americana music, beachfront parties, and unforgettable...
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The Lower Keys
40th Annual Island Art Fair
Hosted by the Lower Keys Chamber of Commerce, the Island Art Festival is a free, family-friendly event celebrating local creativity and community...
SOMO Storytime with author David L. Sloan IV at Avalon Guesthouse
Southernmost Beach Resort & Guesthouses invites locals and visitors to the Avalon Guesthouse on Sunday, Nov. 29, for the next installment of SOMO...
Key West
Writing a Life: The Building Blocks of Memoir with Janice Gary
Wednesday, December 2, 2026, from 2:00 to 4:00 p.m. Janice Gary teaches the building blocks of memoir at The Studios of Key West, a two-hour workshop...
Key West
Winter Members’ Exhibit: Let the Light In
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December 3 through December 31, 2026, daily from 10:00 a.m. to 4:00 p.m. The Studios of Key West hangs its winter members’ exhibition, Let the Light...
Key West
End of Prohibition Celebration
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Thursday, December 3 through Saturday, December 5, 2026. Key West spends three days marking the one thing the Constitution has only ever done once...
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Key West
It's A Wonderful Live: A Live Radio Play at Waterfront Playhouse
December 3-17, 2026 It’s a Wonderful Life: A Live Radio Play at Waterfront Playhouse brings a festive twist to the holiday season with a creative...
Key West
Scarlet Soirée: A Holiday Affair
Thursday, December 3, 2026, 7:00 to 11:00 p.m. Island Girl Promotions hosts the Scarlet Soirée, a holiday benefit on the rooftop at Celtic Conch...
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Islamorada
Islamorada Sailfish Tournament
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December 4–6, 2026 The Islamorada Sailfish Tournament kicks off the Florida Keys Gold Cup Championship as the first leg of the three-tournament series...
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Key West
First Fridays on Fleming
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Every first Friday of the month from 6 to 9 p.m., Fleming Street in Key West transforms into a lively celebration of island creativity, community, and...
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Key West
Junk in the Trunk: Holiday Re-Gifting Sale
Saturday, December 5, 2026, from 8:00 a.m. to 1:00 p.m. Junk in the Trunk puts a holiday spin on its reuse and repurpose concept with the first of two...
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Marathon
7 Mile SantaCon
Get ready to celebrate the holidays Florida Keys style at the 2026 7 Mile SantaCon in Marathon, Florida! Dress in your most festive holiday gear and...
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Islamorada
Lignumvitae Christmas
Saturday, December 5, 2026 Celebrate the holiday season with a unique island experience at Lignumvitae Christmas, held at Lignumvitae Key Botanical...
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Key West
Rich Vos at Comedy Key West
Dec 3rd - Dec 6, 2026 Rich Vos has four specials on Comedy Central and over 100 television appearances. He has been seen on HBO, HBO Max, Netflix...
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Key West
Steven Rogers at Comedy Key West
Dec 7 - Dec 10, 2025 Steven Rogers is a stand-up comedian known for his unique blend of wit, vulnerability, and sharp observational humor. His comedic...
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Key West
Shooting Star
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December 8, 2026 through January 2, 2027. Settle in for a heartwarming night of theater at Key West's beloved Red Barn Theatre, where Steven Dietz's...
