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 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
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...
Key West
Watercolor & Crayon: Autumn Art for Kids Workshop with Bria Ansara at The Studios of Key West
Nov 15, 2025
Discover creativity in the Florida Keys! Join the "Watercolor Crayon Autumn Art for Kids" workshop with Bria Ansara at The Studios of Key West...
Key West
Clay Monoprinting: Stacey Johnson Hardy at The Studios of Key West
Nov 15, 2025
Discover your creative side in the Florida Keys! Join the "Clay Monoprinting with Stacey Johnson Hardy" workshop at The Studios of Key West. Perfect...
Key West
Day of Conservation
Nov 15, 2025
Third Saturday of Every Month Experience “A Day of Conservation” at the Key West Botanical Garden! Enjoy a native plant sale, composting workshop, and...
Key West
Rams Head Presents: The Garcia Project
Nov 15, 2025
The Garcia Project is a tribute band dedicated to celebrating the soulful music and enduring legacy of the Jerry Garcia Band. Formed by passionate...
Key West
Book Release: Who Is Charlie Jones
Nov 15, 2025
Discover literary magic at Key West BookFest 2025! Join renowned authors, engaging panels, book signings, and lively events in the vibrant Florida...
Key West
Zack Seemiller: This Show Saves Lives at Key West Theater
Nov 16, 2025
Join us for an unforgettable evening in The Backstage Listening Room featuring an intimate acoustic performance by renowned singer-songwriter Zack...
Key West
Golden Girls: The Tribute Show - A Drag Parody at Key West Theater
Nov 16, 2025
An afternoon of hilarious fun with Dorothy, Rose, Blanche, and Sophia! Live scenes with big laughs, musical performances, interactive Golden Girls...
Key West
The Life & Art of Eric Anfinson: A Documentary Film by Cassidy Rast & Odin Wadleigh at The Studios of Key West
Nov 16 - 17, 2025
Experience an exclusive work-in-progress screening of The Life & Art of Eric Anfinson, a powerful new documentary capturing the creative journey of...
Key West
Ann Hampton Callaway at Tennessee Williams Theater
Nov 17, 2025
Ann Hampton Callaway is one of America’s most gifted artists in pop and jazz. A leading champion of the great American Songbook, she’s made her mark...
Key West
No Shoes, Real Songs: Part II (w. David Lowe, CW Colt, Carson Lowe & Kayla Rose) at Key West Theater
Nov 17, 2025
Kick back, take your shoes off, and enjoy an evening of laid-back island tunes at No Shoes, Real Songs: Part II, featuring David Lowe, C.W. Colt...
