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
Marathon
Renewing Our Reefs Together: Reef Renewal 2nd Annual Fundraiser
Feb 20, 2026
Reef Renewal USA’s Second Annual Fundraiser, Renewing Our Reefs Together, sponsored by First Horizon Bank, will take place at Aquarium Encounters on...
The Lower Keys
One Love, One Night at Grimal Grove
Feb 20, 2026
Grimal Grove invites you to take a step into the sounds and tropical vibrations of Jamaica. Featuring a curated menu by award winning chef and One...
Key West
Darcy Cooke Songs & Stories of the Silver Screen
Feb 20, 2026
Glamour, gossip, movies and music. Become a Hollywood insider for the evening, enjoying the songs and backstories of the music that made the movies...
Key West
Feel the Spirit: Generative Poetry Weekend at Elizabeth Bishop House with Rosalind Brackenbury
Feb 20 - 22, 2026
Escape to Key West for a generative poetry weekend (Feb 20–22, 2026) at the restored Elizabeth Bishop House. Led by Rosalind Brackenbury, enjoy small...
Marathon
Stupid Cupid Splash Zone
Feb 21, 2026
Get ready to make a splash this Valentine’s season at the Stupid Cupid Splash Zone in Marathon! This fun, family-friendly water event brings together...
Islamorada
Gigantic Nautical Market
Feb 21 - 22, 2026
Experience the **Upper Keys Rotary Gigantic Nautical Market** in Islamorada at Founders Park (MM 87) on **February 21–22, 2026**—a seaside outdoor...
Key Largo
Flamingos in February: Friends Night Out
Feb 21, 2026
Join the Friends of John Pennekamp Coral Reef State Park and Dagny Johnson for Flamingos in February – Friends Night Out, a fun, social fundraising...
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
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
Into the Light: Drawing Atmosphere & Form
Feb 21, 2026
Explore the expressive possibilities of graphite in this focused drawing workshop led by Priscilla Coote. Designed for artists looking to strengthen...
Key West
Capturing Nature with Printing (on Paper)
Feb 21, 2026
Explore the quiet beauty of botanicals in this hands-on printing workshop led by Dawn Wilkins. Participants will use simple, meditative nature...
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...
Key West
From Baroque to Beyond The Music Room Youth Classical Concert at The Studios of Key West
Feb 22, 2026
Experience Key West culture with The Music Room Youth Classical Concert - an inspiring, free performance directed by Robin Kaplan. Celebrating 45...
Key West
Key West Comedy Club Presents: Master Debaters
Feb 22, 2026
Get ready for a night of laughter with Master Debaters, a live comedy event in Key West featuring quick-witted debate, hilarious arguments, and side...
