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 Lime Festival
Jul 1 - 5, 2026
The Key Lime Festival is a vibrant, multi-day celebration held each summer in Key West, Florida, honoring the island’s signature citrus and quirky...
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...
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
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...
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...
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
Key West Paddle Classic
May 9, 2026
Get ready to hit the water for the **29th Annual Key West Paddle Classic** on **May 9, 2026** — one of the East Coast’s premier paddle events and a...
Islamorada
Island Knights 3rd Annual Motorcycle & Car Show
May 9, 2026
Rev up your engines for the Island Knights 3rd Annual Motorcycle & Car Show on Saturday, May 9 from 10 AM to 2 PM at Founders Park in Islamorada...
Key West
Rams Head Presents: 10,000 Maniacs
May 10, 2026
Celebrating over four decades of influential music, 10,000 Maniacs bring their signature blend of poetic lyricism and rich melodies to the stage...
Key West
Dance Factory Presents Threads of Love: A Mother’s Legacy Through Dance
May 10, 2026
Celebrate the beauty of movement and the power of legacy this Mother’s Day at Threads of Love: A Mother’s Legacy Through Dance, a heartfelt...
Key West
The 40th Annual Queen Mother Pageant
May 11, 2026
Celebrate tradition, glamour, and over-the-top fun at the 40th Annual Queen Mother Pageant, presented by John “Ma” Evans and the Key West Theater. A...
Featured
Key West
Sean Patton at Comedy Key West
May 11 - 12, 2026, May 12 - 13, 2026
May 11–12 Sean Patton brings two nights of sharp, globally seasoned stand-up to Comedy Key West on May 11 and 12. A New York–based comedian with roots...
Featured
Key West
Wyatt Cote at Comedy Key West
May 13, 2026, May 14, 2026, May 15, 2026, May 16, 2026
May 13, 14, 15, 16 | 8:30 PM Don’t miss rising stand-up star Wyatt Cote as he brings his sharp, high-energy comedy to Key West for a special multi...
Key West
Tri Knot to Rock at The Key West Theater
May 15, 2026
Experience a night of legendary rock reimagined as Tri Knot takes over the Key West Theater on Friday, May 15th, 2026, delivering electrifying...
Key West
Mile Zeros: Un-Anchored — Screening & Q&A
May 15, 2026
Mile Zeros: Un-Anchored is a new independent comedy series created by Florida Keys filmmakers, bringing a quirky, on-the-water twist to island life...
