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.
See Some Shenanigans
Featured
Key West
Key West Film Festival
Nov 12 - 16, 2025
Key West Film Festival transforms the island into a vibrant destination for film lovers, filmmakers, and critics from around the world. Set against...
Featured
Key West
New Year's Eve Red Shoe Drop
Dec 31, 2025 - Jan 1, 2026
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 2 - 12, 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...
Key West
RAMS HEAD PRESENTS: THE WHEELAND BROTHERS
Nov 8, 2025
Experience the magic of live music in paradise! Join us at Key West Theater for an unforgettable night with The Wallflowers on October 18, 2024. Enjoy...
Key West
Tails on the Trails
Nov 8, 2025
Join the fun at "Tails on the Trails" at the Key West Tropical Forest & Botanical Garden! Enjoy a day of nature, local vendors, and pet-friendly...
The Lower Keys
Boondocks Grill First Annual Fall Festival
Nov 8, 2025
Fall is in the air at Boondocks! Join us on Saturday, November 8th from 11 AM – 3 PM for our FALL FESTIVAL — a Saturday Farmers’ Market packed with...
Key West
Southernmost Youth Orchestra Concert at The Studios of Key West
Nov 9, 2025
Experience the magic of the Southernmost Youth Orchestra! Join us for an inspiring performance by a talented group of young local string musicians...
The Lower Keys
Mini Golf Tournament: Putting for Homes
Nov 9, 2025
Putt for a purpose at the Mini Golf Tournament: Putting for Homes on Sunday, November 9, 2025, from 12:30 p.m. to 3:30 p.m. at Boondocks Grille, Draft...
Key West
Gallery on Greene and The Studios of Key West Present: Cuban Art Tours
Nov 10 - 14, 2025
Would you like to visit the most cutting edge artist studios in Cuba? Have a private opportunity to meet with top internationally recognized museum...
Key West
An Evening in Conversation with Kenny Chesney at Tennessee Williams Theater
Nov 10, 2025
Kenny Chesney went from outside the Knoxville city limits, playing sports and loving music to being elected to the Country Music Hall of Fame...
Key West
72 Hour Film Challenge! at Williams Hall
Nov 11, 2025
Join us for the premiere screening of the 72 Hour Film Challenge—where creativity, caffeine, and chaos collide. Local filmmakers had just three days...
Key West
Rams Head Presents: Elton Dan & The Rocket Band
Nov 12, 2025
Experience the magic of Elton John’s greatest hits with Elton Dan & The Rocket Band at Rams Head in Key West! Enjoy an unforgettable night of music...
Key West
Steve Bjork at Comedy Key West
Nov 12 - 15, 2025
November 12, 13, 14, 15 The Boston Globe recently described Steve Bjork as “one of the top names” in New England stand-up comedy. He’s come a long way...
Key West
Vicki & Laurie - Cabaret at Tennessee Williams Theater
Nov 13, 2025
Still threatening their own brand of trouble, Laurie Breakwell and Vicki Roush storm the Tennessee Williams Cabaret with bold, brassy, and bossy songs...
The Lower Keys
Sugarloaf Showdown
Nov 13 - 15, 2025
The 12th Annual Sugarloaf Showdown, hosted by the Lower Keys Guides Association (LKGA), returns to Sugarloaf Key, November 13–15, 2025, bringing...
Key West
Fooling Buddha
Nov 13, 2025
A witty and magical coming-of-age story about the first “American Buddhist” kid on the block in the 1970s. Combining masterful storytelling with...
Key Largo
Old Highway Run/Walk
Nov 15, 2025
Experience the charm of the Florida Keys at the Old Highway Run! Enjoy scenic ocean views, historic bridges, and vibrant local culture as you run...
Key West
Kaleidoscopia
Nov 15, 2025
Experience Kaleidoscopia in the Florida Keys—a vibrant celebration of LGBTQ+ art, music, and culture! Enjoy dazzling performances, interactive...
