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
Sunny Jim: Cayman Days
Settle into the intimate Back Stage Listening Room at the Key West Theater for an evening of island music and storytelling with Sunny Jim: Cayman Days...
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Key West
Sunny Jim: Florida Days
Settle into the intimate Back Stage Listening Room at the Key West Theater for Sunny Jim: Florida Days on October 30, an evening of island-inspired...
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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
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...
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Key Largo
Owl-O-Ween
Celebrate Halloween the wild way at Owl-O-Ween, a family-friendly evening presented by the Florida Keys Wild Bird Center at the Laura Quinn Wild Bird...
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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
Order of the Sleepless Knights Tour
October 28–November 1, 2026. Celebrate the music, stories, and Key West legacy of Jimmy Buffett during the Gathering of the Order of the Sleepless...
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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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Islamorada
Dia De Los Muertos Celebration
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Celebrate Dia de los Muertos with memory, music and dance during a celebration in the colorful Florida Keys Brewing Company beer garden in Islamorada...
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Key West
Catch the Mania Trivia
Every Monday in November 2026, November 2, 9, 16, 23 and 30, from 6:30 to 8:30 p.m. Put your trivia knowledge to the test during Catch the Mania...
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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
Bella Italia: Chef's Encore Dinner Series
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Friday, November 6, 2026, from 6 to 8 p.m. Savor the flavors of Italy during Bella Italia, the November edition of the Chef’s Encore Dinner Series at...
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Key West
34th Annual Zonta ABC 5K & 10K Run/Walk
Saturday, November 7, 2026. Run or walk for an important local cause during the 34th Annual Zonta ABC 5K & 10K Run/Walk in Key West. ABC stands for...
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Key Largo
Key Largo SCUBAPRO + Mote Community Coral Reef Full Dive Restoration Program
Saturday, November 7, 2026, in Key Largo. Go beyond observing the reef and experience the science behind its recovery during Mote Marine Laboratory’s...
