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
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...
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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...
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
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
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
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
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
Flamy Grant in Concert
Jan 6 - 7, 2026
The Studios of Key West presents Flamy Grant, the award-winning drag artist and singer-songwriter whose powerhouse vocals, sharp wit, and soulful...
Key West
Rams Head Presents: Los Lobos
Jan 6, 2026
Experience an unforgettable night in the Florida Keys as Rams Head Presents Los Lobos! Enjoy the legendary band’s unique blend of rock, blues, and...
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...
Key West
THE QUEENS OF COUNTRY: PATSY! DOLLY! LORETTA!
Jan 7 - 10, 2026
Christine Mild will return to the Barn with her latest musical special event, “The Queens of Country: Patsy! Dolly! Loretta!”. The show will have only...
Key West
Musical Benefit for Jamaica at William Weech American Legion Post 168
Jan 7, 2026
Escape to Key West for Musical Benefit for Jamaica on Jan 7, 2026 at William Weech American Legion Post 168. Doors 3 PM, show 4 PM. Live ensemble led...
Featured
Key West
Ben Harrison at Key West Theater
Jan 8, 2026, Jan 21, 2026, Feb 5, 2026, Mar 5, 2026, Mar 25, 2026
Show Dates: Jan 8, 21 Feb 5, 17 March 5, 25 IRREVERENT, FUNNY, and FULL OF KEY WEST, Ben is the author of the musicals UNDYING LOVE, EL ISLEÑO: The...
Key West
Edel Rodriguez: WORM: A Cuban American Odyssey
Jan 8 - 29, 2026
WORM: A Cuban American Odyssey The Studios of Key West presents WORM: A Cuban American Odyssey, an exhibition by internationally acclaimed artist and...
