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 West
Bill Steely Presents: Where’s Dave Band at Key West Theater
Apr 27, 2026
Experience true Americana in Key West on April 27, 2026: Where’s Dave Band brings heartfelt country from small‑town stories to the intimate Key West...
Featured
Key West
Key West International Dance Company presents Long Live Lambada!
Apr 28, 2026, Apr 29, 2026, Apr 30, 2026
April 28, 29, 30, 2026 Back by popular demand, this crowd-favorite returns after wowing audiences during our inaugural season. Presented by the Key...
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...
Featured
Marathon
Dolphin Research Center’s Dolphin Sunset Celebration
Apr 29, 2026, May 27, 2026, Jun 24, 2026, Jul 29, 2026, Aug 26, 2026, Sep 30, 2026, Oct 28, 2026, Nov 25, 2026, Dec 16, 2026
An intimate, after-hours experience at Dolphin Research Center in the Florida Keys, this sunset program offers a unique opportunity to connect with...
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...
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...
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...
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...
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...
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...
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...
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
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...
