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 Songwriters Festival
Apr 29 - May 3, 2026
The Key West Songwriters Festival is the largest gathering of its kind in the world, drawing music fans and creators to Key West for five immersive...
Key West
Comedy Key West Presents: Comedy Songwriters Show with Keifer Thompson
Apr 30, 2026
Experience a night of music and laughter in Key West as part of the Songwriter’s Festival, featuring award-winning country artist turned comedian...
Islamorada
Jeff Leonia Reel and Steel Classic
Apr 30 - May 1, 2026
The Live Like Jeff Reel & Steel Classic is an annual Florida Keys fishing and diving tournament held in honor of Captain Jeff Leonia, a beloved local...
Islamorada
I.CARE'S ANNUAL TRASH DERBY
Apr 30 - May 3, 2026
Join I.CARE's Trash Derby in the Florida Keys, April 30–May 3, 2026: three days of sunrise-to-sunset marine debris collection from Key Largo to Key...
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...
The Lower Keys
Reef Relief Paddle Cleanup at Coupon Bight
May 1, 2026
Join Reef Relief on May 1st for a Paddle Cleanup at Coupon Bight Aquatic Preserve, located at 1300 Big Pine Ave, Big Pine Key, FL 33043. In...
Key West
Creative Kickstart with Eric Lapin
May 1, 2026
Jumpstart your creative business with this dynamic workshop led by Eric Lapin at The Studios of Key West. Designed for artists and creatives looking...
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
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
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...
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...
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...
