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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Featured
Key West
New Year's Eve Red Shoe Drop
Dec 31, 2025
Ring in the New Year, Key West-style, with one of the island’s most iconic and flamboyant celebrations — the Red Shoe Drop! As the clock counts down...
Featured
Key West
Key West Literary Seminar (2026)
Jan 8 - 11, 2026
The Key West Literary Seminar is a world-renowned annual event that celebrates the art of storytelling in one of the most inspiring literary...
Featured
Key West
Mile 0 Fest (2026)
Jan 27 - 31, 2026
Experience Mile 0 Fest in the stunning Florida Keys! Enjoy five days of top Texas Red Dirt & Americana music, beachfront parties, and unforgettable...
Featured
Islamorada
Morada Way Third Thursday Art Walk
Nov 20, 2025, Dec 18, 2025, Jan 15, 2026, Feb 20, 2026, Mar 19, 2026, Apr 16, 2026, May 21, 2026, Jun 18, 2026, Jul 16, 2026, Aug 21, 2026, Sep 17, 2026, Oct 15, 2026
Dates: Third Thursday of each month from 6 to 9pm Experience the vibrant Morada Way Arts & Cultural District Art Walk in the Florida Keys! Enjoy local...
Key West
Sloppy Joe’s 32nd Annual Dropping of the Conch Shel
Dec 31, 2025
Experience the vibrant energy of the Florida Keys at Sloppy Joe’s! Enjoy live music, lively events, and unforgettable parties in the heart of Key West...
Key West
New Year's Eve at Sunset Pier
Dec 31, 2025
Ring in the New Year at Sunset Pier in Key West! Enjoy live music, festive drinks, and stunning ocean views as you celebrate under the stars. Don’t...
Marathon
New Year's Eve Dinner and Anchor Drop Party
Dec 31, 2025
Join us for an elegant prix fixe menu featuring seasonal flavors, elevated cuisine, and optional wine pairings—all served in the warm glow of our...
Key West
Great Gatsby NYE 2026 at First Flight Island Restaurant & Brewery
Dec 31, 2025
Ring in 2026 with style at the Great Gatsby NYE in the Florida Keys! Enjoy a glamorous night of live music, dancing, and 1920s-inspired festivities...
Key West
Lowering of the Pirate Wench at Midnight at Schooner Wharf Bar!
Dec 31, 2025
Ring in the New Year at the iconic Lowering of the Pirate Wench at Schooner Wharf Bar in Key West! Join the lively crowd at midnight as a pirate wench...
Featured
Key West
Waterfront Playhouse - What the Constitution Means to Me (Spotlight Series)
Jan 1, 2026, Jan 2, 2026, Jan 3, 2026
Jan 1, 2026 - Jan 3, 2026 Fifteen-year-old Heidi earned her college tuition by winning constitutional debate competitions across the country. In this...
Key West
Polve Vault in Paradise (2026)
Jan 1 - 4, 2026
Experience Pole Vault in Paradise in Key West! Join us for an exciting pole vault competition set against stunning island views. Enjoy a unique blend...
Key Largo
First Day Hike at Dagny Johnson Key Largo Hammock Botanical State Park
Jan 1, 2026
Usher in 2026 with a guided New Year’s Day nature walk at **Dagny Johnson Key Largo Hammock Botanical State Park** on Thursday, January 1, at 9:30 a.m...
Key West
Scott Kirby- 35 Years of Songs & Stories w/ Noah Robertson at Key West Theater
Jan 2 - 3, 2026
Jan 2 & Jan 3 Singer, songwriter, guitarist, storyteller, traveler and road warrior are all words that aptly describe Scott Kirby. Finishing songs...
Key West
Friends of the Key West Library Book Sale
Jan 3, 2026
The Friends of the Key West Library book sale is like none you’ll ever see. Set in the beautiful Library Palm Garden, you will have an opportunity to...
Key Largo
Orange Bowl Swim Classic
Jan 3, 2026
The Orange Bowl Swim Classic is held the first weekend in January and is an integral part of the Orange Bowl events schedule. Jacobs Aquatic Center...
Key West
Ian Maksin: New Album Release Tour at Williams Hall
Jan 3, 2026
Ian Maksin brings his new album Lullaby for the World to Key West’s Williams Hall (Jan 3, 7 PM). His one‑man cello‑orchestra and voice weave global...
Key West
Ulysses Quartet at Tennessee Williams Theater
Jan 4, 2026
The Ulysses Quartet has been praised for their "textural versatility," "grave beauty" and "the kind of chemistry many quartets long for, but rarely...
Key West
Schmaltz & Pepper at Tennessee Williams Theater
Jan 6, 2026
Classy klezmer- chamber music and jazz infused with schmaltz A uniquely virtuosic and entertaining chamber ensemble performing original music inspired...
