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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Each October, Fantasy Fest transforms Key West into a colorful celebration of costumes, creativity, music, and performance. The multi-day festival was...
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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
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
Cathy Rose: Object Lessons at JAG Gallery
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October 7 through November 1, 2026, with an opening reception Wednesday, October 7. JAG Gallery begins its new season with Object Lessons, an...
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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...
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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
Original Works: Piano Concert by Nathan Kelly
Friday, October 9, 2026, from 6 to 8 p.m. Pianist, composer, and arranger Nathan Kelly presents an intimate concert of his original music in the...
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Key West
If The Shoe Fits: Key West National Finals
Saturday, October 10, 2026 at 8:00 PM. The national finals of If The Shoe Fits land in Key West, outside the Bourbon Street Pub and New Orleans House...
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Key West
SOMO Half Marathon & 10K
Sunday, October 11, 2026. Lace up for an island run or lend a hand behind the scenes during the SOMO Marathon, Half Marathon & 10K, a Key West race...
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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
Womankind Greene Street Fundraiser
Join the Key West community on October 14 for a special Greene Street fundraiser benefiting Womankind, a nonprofit health center providing healthcare...
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Key West
National Dessert Day at Key West Cooking Show
October 14, 2026. Celebrate National Dessert Day with a distinctly Key West twist at the Key West Cooking Show, where one of the Florida Keys’ most...
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Key West
Fly Into Fantasy Fest with Tropic Ocean Airways
October 15, 16, 18, 22, 23 and 25, 2026. Skip the Overseas Highway and take to the skies during Fantasy Fest with Tropic Ocean Airways’ nonstop...
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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...
