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
34th Annual Florida Keys Island Fest
Each spring, the Florida Keys Island Fest brings two days of vibrant community celebration to Founders Park in Islamorada. Organized by the Islamorada...
Capturing the Light of Key West: Plein Air Painting
Wednesday, Thursday & Friday, February 18, 19 & 20, 9am – 3pm Capture the distinctive light and atmosphere of Key West in this immersive plein air...
Letters from Max at Fringe Theater
Running February 18–20, Letters from Max by Sarah Ruhl is a tender meditation on art, mentorship, and the beauty of human connection. Based on the...
RAMS HEAD PRESENTS: YACHTLEY CREW
Set sail for smooth sounds and good-time vibes with Yachtley Crew – The Titans of Soft Rock, the world’s premier Yacht Rock band! Dressed in their...
Key West International Dance Company - 'GATE 54B'
February 19th, 20th, 21st, 24th, 25th, 26th, 27th, 28th Experience the vibrant rhythms of Key West International Dance Company in the Florida Keys...
RAMS HEAD PRESENTS: MARTY STUART AND HIS FABULOUS SUPERLATIVES
Experience an unforgettable night in the Florida Keys! Catch Marty Stuart and His Fabulous Superlatives live at the Key West Theater. Enjoy world...
Renewing Our Reefs Together: Reef Renewal 2nd Annual Fundraiser
Reef Renewal USA’s Second Annual Fundraiser, Renewing Our Reefs Together, sponsored by First Horizon Bank, will take place at Aquarium Encounters on...
Feel the Spirit: Generative Poetry Weekend at Elizabeth Bishop House with Rosalind Brackenbury
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...
Darcy Cooke Songs & Stories of the Silver Screen
Glamour, gossip, movies and music. Become a Hollywood insider for the evening, enjoying the songs and backstories of the music that made the movies...
One Love, One Night at Grimal Grove
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...
Carson Lowe Single Release at Key West Theater
Carson Lowe celebrates the release of his new song “The Poets” with a special one-night performance at the Key West Theater: experience his new album...
Rimsky-Korsakov, Mozart,Joachim & Simon at Tennessee Williams Theater
Masterworks III: Rimsky-Korsakov's Capriccio Espagnol with Mozart, Joachim & Simon Featuring Seth Parker Woods, cello Simon Four Black American Dances...
Gigantic Nautical Market
Experience the **Upper Keys Rotary Gigantic Nautical Market** in Islamorada at Founders Park (MM 87) on **February 21–22, 2026**—a seaside outdoor...
CONNECTIONS PROJECT Pop-Up, Key West Art & Craft Festival at Truman Waterfront Park
Join The Connections Project: A Mosaic of the Keys— pop-up event across the Florida Keys celebrating local visual and performing artists. Explore...
Into the Light: Drawing Atmosphere & Form
Explore the expressive possibilities of graphite in this focused drawing workshop led by Priscilla Coote. Designed for artists looking to strengthen...