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
Race World Offshore (2025)
Sports fans with a need for speed can fuel their passion at the Race World Offshore Key West World Championship, set for Sunday through Sunday, Nov. 2...
Key West Film Festival
Key West Film Festival transforms the island into a vibrant destination for film lovers, filmmakers, and critics from around the world. Set against...
Custom House Holiday Concert & Bazaar
Experience the festive spirit at the Holiday Bazaar in the Florida Keys! Enjoy unique gifts from local artisans, live music, delicious treats, and a...
A Positive Step 5K Rudolph Red Nose Run
Join the festive 2025 A Positive Step 5K Rudolph Red Nose Run in Key West on Saturday, Dec. 13! Enjoy a fun, family-friendly race through scenic...
Gay Key West Holiday Lights Trolly Tour
Escape to the Florida Keys! Join us for an unforgettable event featuring local cuisine, live music, and island adventures. Discover the vibrant...
Key West Lighted Boat Parade
The Holidays' Magical Nautical Display of Lights and Creativity. The Judges' Stand is located at Schooner Wharf. A "Not-to-be-Missed" Event.
iPhone Photography and Editing with William Carito
Unlock your creativity in the Florida Keys! Join the "iPhone Photography and Editing" workshop with William Carito at The Studios of Key West. Learn...
Second Annual Pigeon Key Holiday Spectacular
The Second Annual Pigeon Key Holiday Spectacular is a one-day celebration filled with festive activities, seasonal treats, and holiday magic for all...
Key West Triathlon
Experience the thrill of the Key West Triathlon! Swim in crystal-clear waters, bike along scenic oceanfront roads, and run through vibrant Key West...
Intuitive Painting with B. Lucy Stevens
Unleash your creativity in the Florida Keys with "Intuitive Painting with B. Lucy Stevens" at The Studios of Key West! No experience needed—just bring...
Sheriff’s Animal Farm Open House
Visit the family-friendly Monroe County Sheriff’s Animal Farm, open the second and fourth Sundays of each month from 1 to 3 p.m. Animals include a...
MassQing: Paint as Personal Ritual with Daniel Callahan (PEAR)
Experience "MassQing: Paint as Personal Ritual" with artist Daniel Callahan at The Studios of Key West. Discover the transformative power of face...
Theatrical Clown and Puppetry with Donna Oblongata (PEAR)
Experience a whimsical evening in the Florida Keys with "Theatrical Clown and Puppetry" by Donna Oblongata at The Studios of Key West. Delight in...