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
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...
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Key West
RAMS HEAD PRESENTS: DUSTY SLAY THE NEIGHBORHOOD GUY TOUR
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You can take the boy out of the trailer park, but you can’t take the trailer park out of the boy… stand-up comedian Dusty Slay grew up on Lot 8 of a...
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Key West
Junk in the Trunk: Truman Waterfront Community Yard Sale
Saturday, November 21, 2026, from 8:00 a.m. to 1:00 p.m. Junk in the Trunk returns to Truman Waterfront Park for a straight ahead community yard sale...
Key West
4th Annual Pirates & Mermaids Rum Chase
Saturday, November 21, 2026, from 5:00 to 9:00 p.m. The Key West Tropical Forest & Botanical Garden turns its grounds over to an adults-only scavenger...
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Key West
Rams Head Presents: Buena Vista Social Orchestra
The Buena Vista Orchestra brings the timeless sounds of Cuban music to the Key West Theater as part of their 2025 USA Tour. Led by renowned Cuban...
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Key West
Sheriff’s Animal Farm Open House
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Enjoy a fun and memorable family outing at the Monroe County Sheriff’s Animal Farm on Stock Island. Open the second and fourth Sunday of each month...
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Key West
Thanksgiving at Hot Tin Roof
Thursday, November 26, 2026. Hot Tin Roof serves a four-course prix fixe holiday menu that celebrates cherished traditions, built around refined...
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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...
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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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Key West
Black Friday Market: Shopping Extravaganza
Get ready for the ultimate Black Friday shopping experience at the Black Friday Market: Shopping Extravaganza! Join us on Friday, November 28 from 10...
Key West
Writing a Life: The Building Blocks of Memoir with Janice Gary
Wednesday, December 2, 2026, from 2:00 to 4:00 p.m. Janice Gary teaches the building blocks of memoir at The Studios of Key West, a two-hour workshop...
Key West
End of Prohibition Celebration
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Thursday, December 3 through Saturday, December 5, 2026. Key West spends three days marking the one thing the Constitution has only ever done once...
Key West
Winter Members’ Exhibit: Let the Light In
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December 3 through December 31, 2026, daily from 10:00 a.m. to 4:00 p.m. The Studios of Key West hangs its winter members’ exhibition, Let the Light...
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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...
Key West
Scarlet Soirée: A Holiday Affair
Thursday, December 3, 2026, 7:00 to 11:00 p.m. Island Girl Promotions hosts the Scarlet Soirée, a holiday benefit on the rooftop at Celtic Conch...
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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...
