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
Fantasy Fest
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Fantasy Fest is an electrifying, 10-day costume and performance festival held annually in Key West, Florida, each October. First launched in 1979 by...
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Key West
RAMS HEAD PRESENTS: Marty Stuart and His Fabulous Superlatives
Experience an unforgettable evening of country music as Marty Stuart and His Fabulous Superlatives take the stage at the Key West Theater. A five-time...
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Key West
RAMS HEAD PRESENTS: DUSTY SLAY THE NEIGHBORHOOD GUY TOUR
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Get ready for a good time when Dusty Slay brings his unmistakable Southern humor and laid-back storytelling to the stage. Raised on Lot 8 of a mobile...
Featured
Tour de Keys Ride for a Cause
Saturday, November 21, 2026. Pedal through paradise for a purpose during Tour de Keys, a scenic charity cycling adventure that takes riders along the...
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Key West
Rams Head Presents: Buena Vista Social Orchestra
Experience the timeless sounds of Cuba as the Buena Vista Orchestra takes the stage at the Key West Theater, bringing the rhythms and musical...
Key West
Thanksgiving Sunset Dinner Cruise
Thanksgiving Day 2026, boarding for a 5:00 p.m. departure in Key West. Spend Thanksgiving on the water. Sunset Watersports runs a two-hour...
Key West
Thanksgiving Feast at Key West Cooking Show
Thursday, November 26, 2026, with seatings at 11 a.m. and 2 p.m. in Key West. Gather your crew and let the Key West Cooking Show take care of the...
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The Lower Keys
40th Annual Island Art Fair
Celebrate creativity and community at the Island Art Festival, a free, family-friendly gathering hosted by the Lower Keys Chamber of Commerce on Big...
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Key West
Black Friday Market: Shopping Extravaganza
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Saturday, November 28, 2026, from 10 a.m. to 6 p.m. Shop local and celebrate the holiday season during the Black Friday Market: Shopping Extravaganza...
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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...
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Islamorada
Islamorada Sailfish Tournament
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The Islamorada Sailfish Tournament is the first leg of the Florida Keys Gold Cup Championship trifecta. This year, the tournament has a new, two-day...
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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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...
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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...
