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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Featured
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...
Featured
Islamorada
Fall Lecture Series: The Florida Sponge War, Conflict Between Key West and the Gulf Towns
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Wednesday, December 9, 2026. Social hour at 5:00 p.m., lecture at 6:00 p.m. Dr. Rina Bousalis closes the Florida Keys History & Discovery Center’s...
Key West
Distinguished Speaker Series: The Florida Sponge War, Culture, Competition, and Conflict
Thursday, December 10, 2026, from 6:00 to 7:00 p.m. Dr. Rina Bousalis takes the Florida Sponge War to Williams Hall for the Key West Art & Historical...
Featured
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...
Featured
Key West
Shaun Cassidy UNWRAPPED: Songs & Stories For The Holidays
Thursday, December 10, 2026. Get ready to unwrap the holidays Key West style! Grammy-nominated singer, actor, writer, and producer Shaun Cassidy...
Featured
Key West
Holiday Concert & Bazaar
Celebrate the season at the annual Holiday Concert & Bazaar at the Key West Museum of Art & History. This festive community event brings together...
Featured
Islamorada
Islamorada Junior Sailfish Tournament
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Celebrate the 61st Islamorada Junior Sailfish Tournament, a longstanding Florida Keys tradition that brings young anglers and families together for...
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Islamorada
A Night in Monaco: Black & White Formal Gala Casino Night
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Friday, December 11, 2026 | 6–10 p.m. Dress to impress for A Night in Monaco, a Black & White Formal Gala Casino Night hosted by the Florida Keys...
Featured
Key West
The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers
Saturday, December 12, 2026. Get ready to feel like a Refugee and dance down to the Last DJ as The Broken Hearts bring their acclaimed tribute to Tom...
Featured
Key West
18th Annual A Positive Step 5K Rudolph Red Nose Run
Saturday, December 12, 2026. Pull on your loudest holiday pajamas and head for the southern end of Duval Street, because the 18th annual A Positive...
Key West
Southpoint Divers Holiday Morning Reef Dives
Wednesday, December 23, 2026, with four more departures on December 26, December 29, January 1 and January 4. Check-in is 8:00 a.m., the boat leaves...
Marathon
Ice Skating at Isla Bella
Monday, December 28, 2026, from 10:00 a.m. to 6:00 p.m. Isla Bella Beach Resort sets up a pop-up ice rink at Palm Grove, which means skating in the...
Featured
Key West
67th Annual Key West Home Tours
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December 29 to 30, 2026, January 22 to 23, 2027, February 12 to 13, 2027, and March 12 to 13, 2027, from 1:00 to 4:00 p.m. each day. Ever strolled...
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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...
Marathon
New Year's Eve Fireworks at Isla Bella
Thursday, December 31, 2026. Isla Bella Beach Resort closes out the year with a fireworks show over the water at Mile Marker 47 in Marathon, alongside...
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Key West
The Restless Natives: Macon, Georgia's tribute to The Allman Brothers Band
Celebrate the music and legacy of The Allman Brothers Band with The Restless Natives, a Macon, Georgia-based tribute band dedicated to recreating the...
