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
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...
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Key West
Burgers & Buffet Tunes: A Tribute Show at Comedy Key West
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There are plenty of places to enjoy lunch in Key West, but only one invites you to dine with a legend. Burgers & Buffett Tunes at Comedy Key West is a...
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Marathon
MCT Children's Summer Theatre Presents Dare to Dream Jr.
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July 10–11, 2025 – 7:00 p.m. July 12, 2025 – 3:00 p.m. Young performers from Marathon Community Theatre step into the spotlight for Disney’s Dare to...
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Key West
Junk in the Trunk: Fantasy Fest Costume Swap
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Saturday, October 17, 2026, from 8 a.m. to 1 p.m. The Truman Waterfront Community Yard Sale, better known as Junk in the Trunk, returns for its fall...
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The Lower Keys
Open Air Market at Boondocks
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Every Saturday from 9 a.m. to 2 p.m., Boondocks Open-Air Market brings island flavor, local creativity, and tropical charm to Mile Marker 27.5 on...
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Key West
Prime of Life Yoga
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Reconnect with your body, mind, and the natural beauty of Key West during Prime of Life Yoga at the Key West Tropical Forest & Botanical Garden. Held...
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Islamorada
Florida Keys Farmers Market
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Spend your Sunday soaking up local flavor at the Florida Keys Farmers Market in Islamorada. Held every Sunday from 10 a.m. to 3 p.m. in the parking...
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Marathon
Children's Tours & Concert Series at Crane Point Museum & nature Center
Select dates throughout 2027: January 11 and 25; February 8 and 22; March 22; April 8, 13, 15 and 29; May 20; June 14 and 28; July 12; August 23; and...
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Islamorada
Mote Marine Laboratory Trivia Night at Florida Keys Brewing Company
Monday, October 19, 2026, from 7:30 to 9:30 p.m. Grab a drink, gather your smartest friends, and put your marine knowledge to the test during Mote...
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Key West
Glow Hours at Hugh’s Views
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Every Monday and Tuesday, experience Glow Hours at Hugh’s View in Key West, a one-of-a-kind rooftop evening set above The Studios of Key West. Take in...
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Islamorada
Cortadito: A Tribute to the Buena Vista Social Club
Monday, October 19, 2026, at 6 p.m. Experience the rhythms of traditional Cuban music when Cortadito brings its tribute to the legendary Buena Vista...
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Key West
Monday Night Jazz Jams
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Kick off the week with the smooth sounds of Monday Night Jazz Jams at the William Weech American Legion Post 168 in Key West. Held every Monday from 8...
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Key West
The Greatest Hits Pool Party
Tuesday, October 20, 2026, from noon to 4 p.m. Dress like an icon and sing like a legend during the Greatest Hits Pool Party at Winslow’s Bungalows...
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Key West
TUTU SALSA SESSIONS
Tuesday, October 20, 2026. Celebrate one of Fantasy Fest’s most colorful traditions during Tutu Tuesday at Southernmost Beach Café, where beachfront...
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Key West
Rum Revelations: A Cocktail Adventure
Available on select dates October 20–24 and October 27–31, 2026. Mix, shake, and sip your way through the world of rum during Rum Revelations: A...
