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
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...
Key West
CONNECTIONS PROJECT Pop-Up, Key West Art & Craft Festival at Truman Waterfront Park
Feb 21 - 22, 2026
Join The Connections Project: A Mosaic of the Keys— pop-up event across the Florida Keys celebrating local visual and performing artists. Explore...
Islamorada
Gigantic Nautical Market
Feb 21 - 22, 2026
Experience the Upper Keys Rotary Gigantic Nautical Market in Islamorada (Founders Park, MM 87) Feb 21–22, 2026 — a seaside outdoor boat show, gigantic...
Key West
Key West Art & Craft Festival
Feb 21 - 22, 2026
Experience the vibrant art scene of the Florida Keys at the Key West Art Center! Discover stunning local artwork, meet talented artists, and enjoy a...
Key West
Rimsky-Korsakov, Mozart,Joachim & Simon at Tennessee Williams Theater
Feb 21, 2026
Masterworks III: Rimsky-Korsakov's Capriccio Espagnol with Mozart, Joachim & Simon Featuring Seth Parker Woods, cello Simon Four Black American Dances...
Key West
Garrison Keillor and Erica Rhodes: “The Crazy Uncle and His Sensible Niece" at Key West Theater
Feb 22, 2026
Experience an unforgettable evening in the Florida Keys with legendary storyteller Garrison Keillor at the Key West Theater! Enjoy humor, music, and...
Key West
RAMS HEAD PRESENTS: BIG BAD VOODOO DADDY AT KEY WEST THEATER
Feb 22, 2026
Experience Big Bad Voodoo Daddy’s electrifying matinee at the historic Key West Theater — a 32-year swing-revival sensation delivering upbeat horns...
Key West
Lower Keys Rotary Kids Fishing Tournament
Feb 22, 2026
Experience the best of the Florida Keys at the Lower Keys Rotary’s annual event! Don’t miss this chance to celebrate community and the Keys’ laid-back...
Key West
Library Speaker Series: Ruth Reichl
Feb 23, 2026
Celebrate the magic of books, food, and community at the Friends of the Key West Library Fundraising Gala on Monday, February 23, 2026. The evening...
Key West
A FEAST OF WORDS AND FLAVORS WITH RUTH REICHL
Feb 23, 2026
Join bestselling food writer Ruth Reichl for an elegant evening in Key West—an intimate interview and post-talk Palm Garden reception with tropical...
Marathon
Hermitage Trio with Violist Jordan Bak at Marathon High School PAC
Feb 23, 2026
Experience the Grammy‑nominated Hermitage Piano Trio with award‑winning violist Jordan Bak in Marathon on Feb 23, 2026 at Marathon High School...
Key Largo
Hermitage Trio with Violist Jordan Bal at Coral Shores High School PAC
Feb 24, 2026
Treat yourself to an elegant Keys evening: Grammy‑nominated Hermitage Piano Trio with award‑winning violist Jordan Bak performs Feb 24, 2026 at 7:30...
Key West
Key West International Dance Company - 'GATE 54B'
Feb 24 - 28, 2026
This is an exciting and innovative contemporary tango show, featuring internationally known tango dancers, in the unlikely setting of Newark's Liberty...
Featured
Key West
AND THE WORLD GOES ROUND at Red Barn Theater
Feb 24, 2026, Feb 25, 2026, Feb 26, 2026, Feb 27, 2026, Feb 28, 2026, Mar 1, 2026, Mar 2, 2026, Mar 3, 2026, Mar 4, 2026, Mar 5, 2026, Mar 6, 2026, Mar 7, 2026, Mar 8, 2026, Mar 9, 2026, Mar 10, 2026, Mar 11, 2026, Mar 12, 2026, Mar 13, 2026, Mar 14, 2026, Mar 15, 2026, Mar 16, 2026, Mar 17, 2026, Mar 18, 2026, Mar 19, 2026, Mar 20, 2026, Mar 21, 2026
Show Dates: Feb 24 - Mar 21, 2026 An intimate musical revue celebrating the extraordinary work of the composer and lyricist of (among others) “Chicago...
Key West
RAMS HEAD PRESENTS: DMTB: THE DAVE MATTHEWS TRIBUTE BAND
Feb 25, 2026
DMTB is a celebration of the music of the Dave Matthews Band - a time machine to a funky tea party in the 90’s, a boisterous era of tape trading, sing...
Marathon
Dolphin Sunset Celebration
Feb 25, 2026
Join the Dolphin Research Center’s Dolphin Sunset Celebration in the Florida Keys: exclusive after-hours access, intimate dolphin interactions with...
