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
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...
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...
Marathon
20th Annual Tom Thumb Marathon Bull and Cow Dolphin Tournament
May 1 - 3, 2026
The Marathon Offshore Bull & Cow Dolphin Tournament is one of the Florida Keys’ premier offshore fishing competitions, bringing anglers together for a...
Marathon
Grouper Opener Party
May 1, 2026
The Grouper Opener Party is a lively waterfront celebration marking the start of Florida’s highly anticipated grouper season. Held at Hawks Cay Resort...
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
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...
Marathon
XGLOsive Pickleball Party
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...
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
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...
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
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
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
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...
