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
Race World Offshore (2025)
Nov 2 - 9, 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...
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...
Key West
Custom House Holiday Concert & Bazaar
Dec 12, 2025
Experience the festive spirit at the Holiday Bazaar in the Florida Keys! Enjoy unique gifts from local artisans, live music, delicious treats, and a...
Key West
A Positive Step 5K Rudolph Red Nose Run
Dec 13, 2025
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...
Key West
Gay Key West Holiday Lights Trolly Tour
Dec 13, 2025
Escape to the Florida Keys! Join us for an unforgettable event featuring local cuisine, live music, and island adventures. Discover the vibrant...
Key West
Key West Lighted Boat Parade
Dec 13, 2025
The Holidays' Magical Nautical Display of Lights and Creativity. The Judges' Stand is located at Schooner Wharf. A "Not-to-be-Missed" Event.
Key West
iPhone Photography and Editing with William Carito
Dec 13 - 14, 2025
Unlock your creativity in the Florida Keys! Join the "iPhone Photography and Editing" workshop with William Carito at The Studios of Key West. Learn...
Marathon
Second Annual Pigeon Key Holiday Spectacular
Dec 13, 2025
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
Key West Triathlon
Dec 14, 2025
Experience the thrill of the Key West Triathlon! Swim in crystal-clear waters, bike along scenic oceanfront roads, and run through vibrant Key West...
Key West
Intuitive Painting with B. Lucy Stevens
Dec 14, 2025
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...
Key West
Sheriff’s Animal Farm Open House
Dec 14 - Sep 14, 2025
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...
Key West
MassQing: Paint as Personal Ritual with Daniel Callahan (PEAR)
Dec 19, 2025
Experience "MassQing: Paint as Personal Ritual" with artist Daniel Callahan at The Studios of Key West. Discover the transformative power of face...
Key West
Theatrical Clown and Puppetry with Donna Oblongata (PEAR)
Dec 20 - 21, 2025
Experience a whimsical evening in the Florida Keys with "Theatrical Clown and Puppetry" by Donna Oblongata at The Studios of Key West. Delight in...
