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
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
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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Marathon
Marathon Yacht Club Game Day Fundraiser
Wednesday, October 21, 2026, beginning at 11 a.m. Gather around the tables for a day of friendly competition at the Marathon Yacht Club, all while...
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Key West
LUV2GLOW: Liquid Frequency
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Get ready to light up the night at LUV2GLOW: Liquid Frequency, a two-night electronic and dance music experience taking over Rick’s Key West on...
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Key West
Heels For All with Paula Ali
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Wednesday, October 21 and Thursday, October 22, 2026, from 1 to 2:30 p.m. Explore movement, character, and self-expression during Heels For All, a two...
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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
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
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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Islamorada
Treasure Treat Night
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...
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Key West
Photography Masterclass with Frank Stewart
Friday, October 23, 2026, from 1 to 3:30 p.m. Photographers can receive in-depth feedback on their work during a Portfolio Review with acclaimed...
Key West
Southernmost Playboy House - Beach Bunny Pool Party Bash
Friday, October 23, 2026, from 10:30 a.m. to 5:00 p.m. The Southernmost House throws an oceanfront, adults only pool party during Fantasy Fest, billed...
