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
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
Hedwig and the Angry Inch at Waterfront Playhouse
October 15-23, 2026 Hedwig and the Angry Inch opens Waterfront Playhouse’s 88th season with a bold and electrifying rock musical experience presented...
Key West
LUV2GLOW: Liquid Frequency
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Get ready to light up the night at LUV2GLOW: Liquid Frequency, a high-energy two-night electronic and dance music event taking over Rick's Key West on...
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Key West
Rams Head Presents: Garrison Keillor and Erica Rhodes – The Crazy Uncle and His Sensible Niece
Settle in for an evening of storytelling, laughter, and quick-witted comedy as Garrison Keillor and Erica Rhodes take the stage for The Crazy Uncle...
Key West
Sunny Jim: Cayman Days
Settle into the cozy Back Stage Listening Room at the Key West Theater for an intimate evening of island music and storytelling with Sunny Jim: Cayman...
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Key West
Will Kimbrough Live at the Key West Theater
Experience an intimate evening of exceptional songwriting and musicianship as Will Kimbrough takes the stage at the Key West Theater. A respected...
Key West
Sunny Jim: Florida Days
Return to the intimate Back Stage Listening Room at the Key West Theater for Sunny Jim: Florida Days on October 30, a heartfelt companion to the...
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Key West
Rams Head Presents: Buffett Through the Years
Celebrate the music, stories, and island spirit of Jimmy Buffett with Buffett Through the Years, a live tribute show at the Key West Theater featuring...
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Key West
Jim Morris Tribute
Celebrate the music and enduring legacy of beloved Southwest Florida singer-songwriter Jim Morris with a special tribute performance by the Tropicool...
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Key West
Texas Trop Rock: Jerry Diaz, Dan Sullivan, Jonas Lorence Band
Get ready for a night of coastal sounds and laid-back energy as Texas Trop Rock brings Jerry Diaz, Dan Sullivan, and the Jonas Lorence Band together...
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Key West
Race World Offshore
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Feel the need for speed at the Race World Offshore Key West World Championship, when the turquoise waters surrounding Key West become the setting for...
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Key West
Killer Prom: A Tubular Interactive Murder Mystery Comedy
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Step back into the ’80s for a totally tubular night of mystery, comedy, and audience participation when Gold Murder Presents Killer Prom: A Tubular...
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Key West
Rams Head Presents: The Ocean Blue
Step back into the shimmering sounds of alternative rock and indie pop as The Ocean Blue brings decades of melodic songwriting and fan favorites to...
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Key West
Bruce Cockburn & Livingston Taylor at Key West Theater
Experience an exceptional evening of songs, stories, and masterful musicianship as acclaimed singer-songwriters Bruce Cockburn and Livingston Taylor...
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Key West
Destroying David – Waterfront Playhouse (Spotlight Series)
November 12-14, 2026 Destroying David at Waterfront Playhouse launches the Spotlight Series with a thought-provoking and immersive theatrical...
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Key West
A Tribute to the Songs of Pete & Wayne
Key West Theater | 512 Eaton Street, Key West Celebrate the songs, stories, and unmistakable humor of a beloved Key West duo with A Tribute to the...
