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
Islamorada
34th Annual Florida Keys Island Fest
Mar 28 - 29, 2026
Each spring, the Florida Keys Island Fest brings two days of vibrant community celebration to Founders Park in Islamorada. Organized by the Islamorada...
Key West
Capturing the Light of Key West: Plein Air Painting
Feb 18 - 20, 2026
Wednesday, Thursday & Friday, February 18, 19 & 20, 9am – 3pm Capture the distinctive light and atmosphere of Key West in this immersive plein air...
Featured
Key West
Letters from Max at Fringe Theater
Feb 18, 2026, Feb 19, 2026, Feb 20, 2026
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...
Key West
RAMS HEAD PRESENTS: YACHTLEY CREW
Feb 18, 2026
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
Key West International Dance Company - 'GATE 54B'
Feb 19 - 21, 2026
February 19th, 20th, 21st, 24th, 25th, 26th, 27th, 28th Experience the vibrant rhythms of Key West International Dance Company in the Florida Keys...
Key West
RAMS HEAD PRESENTS: MARTY STUART AND HIS FABULOUS SUPERLATIVES
Feb 19, 2026
Experience an unforgettable night in the Florida Keys! Catch Marty Stuart and His Fabulous Superlatives live at the Key West Theater. Enjoy world...
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...
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...
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...
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
Carson Lowe Single Release at Key West Theater
Feb 20, 2026
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...
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...
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 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
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...
