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
Key West Pride 2026
Jun 3 - 7, 2026
Every June, Key West Pride turns the island into a vibrant, inclusive festival full of color, community, and celebration. This weeklong event welcomes...
Key West
Talk Derby to Me! at The Gardens Hotel
May 2, 2026
Celebrate the Kentucky Derby in style at “Talk Derby to Me!” at The Gardens Hotel in Key West on Saturday, May 2 from 5:30–7:30 p.m. This lively...
The Lower Keys
Lower Keys Rotary Derby Day Roundup
May 2, 2026
Experience the best of the Florida Keys at the Lower Keys Rotary’s signature event! Enjoy live music, delicious local food, unique vendors, and family...
Key West
One Night of Queen at Tennessee Williams Theater
May 3, 2026
One Night of Queen: a 2-hour, high-energy tribute starring Freddie Mercury impersonator Gary Mullen & The Works. Relive Queen’s iconic hits and...
Key West
3rd Annual Run for Rhonda
May 3, 2026
Join the 3rd Annual Run for Rhonda, a fun and energetic community event celebrating fitness, friendship, and giving back. This family-friendly race...
Featured
National Travel & Tourism Week/America 250 Kickoff
May 4, 2026
Join us in Big Pine Key for a one-of-a-kind community celebration kicking off National Travel & Tourism Week and America 250! On Monday, May 4 from 11...
Marathon
Margaritas for Mutts
May 5, 2026
Celebrate Cinco de Mayo in the Florida Keys with a tail-wagging twist at Margaritas for Mutts, a fun-filled, dog-friendly event at Dockside Boot Key...
Key West
Community Foundation of the Florida Keys Annual Meeting & 30th Anniversary Celebration
May 6, 2026
This year, the Community Foundation of the Florida Keys celebrates 30 years of connecting people, resources, and needs through philanthropy. For three...
Featured
Key West
Eddie Gossling at Comedy Key West
May 6 - 9, 2026, May 7 - 10, 2026, May 8 - 11, 2026, May 9 - 12, 2026
May 6, 7, 8, 9 Eddie Gossling brings four nights of seasoned, high-energy stand-up to Comedy Key West, May 6 through 9. A comedy veteran with more...
Key West
Key West Playwrights Festival
May 7 - 8, 2026
May 7 & 8, 2026 at 7:00 PM — Experience an engaging evening of original short plays at the Key West Playwrights Festival, held at Williams Hall, 729...
Key West
Happy Birthday Harry!
May 8, 2026
Celebrate President Harry S. Truman's birthday on the lawn of the Truman Little White House in Key West! Free and open to the public on Friday, May 8...
Marathon
20th Annual Mother's Day Dolphin Tournament
May 8 - 9, 2026
Celebrate Mother's Day in the Florida Keys at the 20th Annual Mother's Day Dolphin Tournament in Marathon, May 8–9, 2026. Fish for a cause, compete...
Key West
Menendez Miler 5K Run/Walk
May 9, 2026
The Menendez Miler 5K Run/Walk is a scenic community race in Key West that takes place at Truman Waterfront Park, Southard Street & Butler Boulevard...
Key West
Reef Relief Conch Classic
May 9, 2026
Join the First Annual Conch Classic, a fun, coed 4v4 beach volleyball tournament at Higgs Beach, Key West on May 9, 2026. Enjoy friendly competition...
Key West
George Thorogood & The Destroyers w/ The Marshall Tucker Band at Coffee Butler Amphitheater
May 9, 2026
George Thorogood & The Destroyers hit the stage for a high-energy night of classic rock that fans won’t forget. With a career spanning more than five...
