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
Key West History Through Five Craft Cocktails
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Available October 20–24 and October 27–31, 2026, from 5 to 7 p.m. Raise a glass to Key West’s colorful past during Key West History Through Craft...
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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
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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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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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
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...
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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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Key West
Hemingway in a Funny Way at Comedy Key West
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Raise a glass to one of Key West’s most legendary literary figures during this playful tribute to Ernest Hemingway at Comedy Key West. Led by comedian...
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Key West
Arts & Drafts
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Get creative midweek with Arts & Drafts at The Retro Room in Key West, held every Wednesday from 7 to 9 p.m. This relaxed, social art night pairs a...
Key West
Slow Passage of Time: A Culinary Experience in the Oldest House
Thursday, October 29, 2026, beginning at 6:00 p.m. The Old Island Restoration Foundation opens the Oldest House Museum after hours for a five-course...
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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
Key West Farmers Market
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Discover the vibrant Florida Keys Farmers Market, where fresh local flavors, handmade treasures, and island charm come together in a lively open-air...
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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 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
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...
