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
Writing Character from Setting with CJ Hauser (PEAR)
May 20, 2026, May 21, 2026
Wednesday & Thursday, May 20-21, 12 –1pm Explore the powerful connection between place and personality in this generative writing workshop with...
Key West
Once There Was a Railroad by Wayne Garcia
May 22, 2026
“Once There Was a Railroad” by master woodcarver Wayne Garcia brings the remarkable story of Henry Flagler’s Overseas Railroad to life through a...
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...
The Lower Keys
Carved Flamingo Platter Workshop
May 24, 2026
Create a stunning, tropical-inspired serving piece in this hands-on ceramic workshop where you’ll design a carved flamingo platter using the beautiful...
Marathon
Sunset Celebration at Dolphin Research Center
May 27, 2026
Experience the magic of the Florida Keys at Dolphin Research Center’s Dolphin Sunset Celebration. Join on May 27, 6:30–7:00 PM at the Dolphin Research...
Featured
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 Largo
Skippers Dolphin Tournament (2026)
May 29 - 31, 2026
Experience the excitement of Skippers Tournaments in the beautiful Florida Keys! Enjoy world-class fishing, live music, delicious food, and vibrant...
Featured
Marathon
Indoor Rummage Sale at Kirk of the Keys
May 29, 2026, May 30, 2026
Friday, May 29th from 4:30pm - 7:00pm and Saturday May 30th from 8am - 1pm. Shop for a great cause at this Indoor Rummage Sale at 8877 Overseas Hwy in...
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...
Islamorada
Don Hawley Tarpon Fly Tournament
Jun 1 - 5, 2026
Don Hawley Invitational Tarpon Fly Tournament returns to Islamorada June 1–5, 2026, continuing one of the Florida Keys’ most respected traditions in...
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...
Key Largo
Coralpalooza 2026
Jun 4 - 6, 2026
Join Coralpalooza in the Florida Keys for a hands‑on World Oceans Day celebration—three days of reef restoration where leisure travelers join half‑day...
The Lower Keys
Lower Keys Chamber of Commerce 33rd Annual Dolphin Tournament (2026)
Jun 5 - 7, 2026
Get ready for the 2026 Dolphin Tournament in the Lower Keys — a fishing event open to anglers of all levels targeting prized dolphin (mahi-mahi)! The...
Key West
Bertha: Grateful Drag at Key West theater
Jun 5, 2026
Join BERTHA: GRATEFUL DRAG — an all-star, queer and allied East Nashville tribute band in wigs and full face, fronted by a harmony trio and backed by...
