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
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 Largo
Nick Sheahan Dolphin Rodeo (2026)
May 1 - 3, 2026
Join us in the beautiful Florida Keys for the Nick Sheahan Dolphin Rodeo, a premier fishing event supporting local scholarships. Enjoy world-class...
Featured
Key West
Doug Benson at Comedy Key West
May 1 - 2, 2026, May 2 - 3, 2026
May 1–2, 2026 Doug Benson brings two days of nationally recognized stand-up comedy to Comedy Key West. A legendary comedian, actor, and podcast host...
Marathon
XGLOsive Pickleball Party & Play
May 2, 2026
Experience a high-energy GLO Pickleball Party at Hawks Cay Resort on Duck Key, where the courts come alive under the lights for a fun, social night of...
Featured
Marathon
Keys Together Spring Festival
May 2, 2026
Join us for a celebration of our island communities at Oceanfront Park in Marathon, from 11am-6pm. This family-friendly event will have live music...
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 2, 2026
One Night of Queen is a touring 2-hour stage show, paying tribute to the stage theatrics and music of Queen. It is performed by Gary Mullen & The...
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...
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...
