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...
Featured
Key West
You’re a Good Man, Charlie Brown – Red Barn Theatre
May 1, 2026, May 2, 2026, May 3, 2026
May 1-3, 2026 A heartwarming musical comes to life at the Red Barn Theatre with You’re a Good Man, Charlie Brown, a charming production based on...
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...
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
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...
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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
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
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...
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
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...
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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...
Key West
Salute to Service 5K Run & Walk
May 24, 2026
Celebrate Memorial Day weekend in Key West at the Salute to Service 5K Run & Walk at The Marker Resort on Sunday, May 24, 2026. Starting and finishing...
Key West
36th Annual Schooner Wharf Minimal Regatta
May 24, 2026
Get ready for a splash-filled afternoon at one of Key West’s most unique and entertaining traditions. Participants build their own boats using a...
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Key West
John Caparulo at Comedy Key West
May 28 - 31, 2026, May 29 - Jun 1, 2026, May 30 - Jun 2, 2026, May 31 - Jun 3, 2026
May 28, 29, 30, 31 John Caparulo brings four nights of razor-sharp stand-up to Comedy Key West, May 28 through 31. Known for his unmistakable...
Key West
Key West Pride Follies at Key West Theater
May 30, 2026
Key West Pride presents the Key West Pride Follies on Saturday, May 30 at the Key West Theater. This lively variety show returns as a long-standing...
Featured
Key West
Dan Soder at Comedy Key West
Jun 1 - 2, 2026, Jun 2 - 3, 2026
June 1 & 2 Dan Soder takes the stage at Comedy Key West for two nights of sharp, high-energy stand-up on June 1 and 2. A New York City–based comedian...
