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.
See Some Shenanigans
Featured
Key West
An Evening of Storytelling & Comedy with Stormy Daniels
May 22, 2026, May 23, 2026
Friday, May 22 & Saturday, May 23, 2026 | 8:00 PM Step into a bold and unfiltered night of storytelling comedy as Stormy Daniels takes the stage in...
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...
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...
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...
Key West
Fringe Theater Presents: The Ladies in the Orange Grove
May 28, 2026
Summer Fringe presents a reading of The Ladies in the Orange Grove by playwright David Schmitt, a gripping family saga where sibling rivalry spirals...
Islamorada
Pasta + Taylor Hale Collaborative Painting Release Party
May 28, 2026
Celebrate the release of a one-of-a-kind collaborative painting by Islamorada artists Pasta Pantaleo and Taylor Hale at The Hale Gallery. Years in the...
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
Green Turtle Comedy Club Presents Carl Rimi
May 30, 2026
Get ready to laugh at the Green Turtle Comedy Club Presents Carl Rimi, a one-of-a-kind pop-up comedy experience at the iconic Green Turtle Inn...
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...
