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.
See Some Shenanigans
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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
Shooting Star
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December 8, 2026, through January 2, 2027. Settle in for a heartwarming night of theater as Steven Dietz’s romantic comedy Shooting Star opens the Red...
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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
Personal Effects at Fringe Theater
Dec 9 - Dec 13, 2025 Experience the world premiere of Personal Effects by local playwright Chris Moore, running December 9–13. When the adult children...
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Key West
Shaun Cassidy UNWRAPPED: Songs & Stories For The Holidays
Thursday, December 10, 2026, at 8 p.m. Celebrate the season with Shaun Cassidy as he brings his new holiday show, UNWRAPPED: Songs & Stories For The...
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Key West
Holiday Concert & Bazaar
Friday, December 11, 2026, from 5 to 8 p.m. Celebrate the season during the Annual Holiday Concert & Bazaar at the Key West Museum of Art & History at...
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Islamorada
A Night in Monaco: Black & White Formal Gala Casino Night
Friday, December 11, 2026, from 6 to 10 p.m. Dress in your finest black and white attire for A Night in Monaco, a formal gala and casino night hosted...
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Islamorada
Islamorada Junior Sailfish Tournament
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December 11–13, 2026. Celebrate more than six decades of youth sportfishing during the 61st Annual Islamorada Junior Sailfish Tournament, a Florida...
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Key West
The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers
Saturday, December 12, 2026, at 8 p.m. Celebrate the music and legacy of Tom Petty when The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers...
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Key West
18th Annual A Positive Step 5K Rudolph Red Nose Run
Saturday, December 12, 2026, at 8 a.m. Pull on your most festive holiday pajamas and head to the southern end of Duval Street for the 18th Annual A...
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Key West
67th Annual Key West Home Tours
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December 29–30, 2026 | January 22–23, February 12–13 & March 12–13, 2027 1–4 p.m. | Key West Ever wandered through Key West and wondered what lies...
Key West
New Year's Eve Red Shoe Drop
Ring in the New Year, Key West-style, with one of the island’s most iconic and flamboyant celebrations — the Red Shoe Drop! As the clock counts down...
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Key West
The Restless Natives: Macon, Georgia's tribute to The Allman Brothers Band
Friday, January 1, 2027, at 8 p.m. Celebrate the music and legacy of The Allman Brothers Band when The Restless Natives bring the sound of Southern...
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Key West
For the Love of Country
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**January 5 through January 9, 2027**. Get ready to two-step your way into the new year as Red Barn favorite Christine Mild returns to Key West with...
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Key West
Ben Harrison in Concert
Tuesday, January 5, 2027, at 7 p.m., with six additional performances through April. Key West singer-songwriter, author, playwright, and storyteller...
