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
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...
Islamorada
Brothers of Others: Happy Halloween at Lorelei
Saturday, October 31, 2026, from 5:00 to 9:00 p.m. Brothers of Others play Halloween night at the Lorelei Restaurant & Cabana Bar, bayside at Mile...
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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
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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Islamorada
The Masquerade on the Bay at Pierre’s
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Step into a night of mystery, music and waterfront luxury at Pierre’s at Morada Bay in Islamorada for an unforgettable Halloween celebration at The...
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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
Charcoal Portrait Drawing with Shannon Martin Perkins
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Wednesdays, November 4, 11 and 18, and December 2, 2026, from 5 to 7 p.m. Develop your portrait drawing skills during a four-session course with local...
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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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Islamorada
Forward-Facing Sonar in Florida Bay
Friday, November 6, 2026, from 5:30 to 8 p.m. Join anglers, fishing guides, scientists, conservation professionals, and community members for an...
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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
First Fridays on Fleming
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Every first Friday of the month from 6 to 9 p.m., Fleming Street in Key West transforms into a lively celebration of island creativity, community, and...
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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 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...
