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
Islamorada
Swim for Alligator Lighthouse
-
Dive into an unforgettable adventure in the Florida Keys during the Alligator Lighthouse Swim, an exhilarating open-water challenge surrounded by...
Featured
Key West
CFK Pentathlon Swim Meet & Key West Open Water Swim (2026)
-
Dive into the clear, warm waters of Key West during the Open Water Swims at Higgs Beach, held following the start of The College of the Florida Keys...
Featured
Key Largo
Science Saturdays: Citizen Science Fish ID
September 5, 2026, at 11 a.m. Turn your love of the underwater world into real marine science during Science Saturdays: Citizen Science Fish ID at the...
Featured
Marathon
Heroes Salute 5K Run/Walk
-
Saturday, September 5, 2026 | 7–8:30 a.m. | Duck Key Lace up and salute the heroes at the Heroes Salute 5K Run/Walk, kicking off the 18th Annual...
Featured
Key West
3rd Annual Parrots & Margaritas 5K Run/Walk
Labor Day Weekend | 8 A.M. | Key West Kick off Labor Day weekend with a little exercise and a lot of island spirit at the 3rd Annual Parrots &...
Featured
The Lower Keys
Open Air Market at Boondocks
-
Every Saturday from 9 a.m. to 2 p.m., Boondocks Open-Air Market brings island flavor, local creativity, and tropical charm to Mile Marker 27.5 on...
Featured
Key West
Prime of Life Yoga
-
Reconnect with your body, mind, and the natural beauty of Key West during Prime of Life Yoga at the Key West Tropical Forest & Botanical Garden. Held...
Featured
Key West
Occupational Hazard: The First Coral Reefers
Step into the creative heart of Old Town for Occupational Hazard: The First Coral Reefers, a special two-show engagement at the Key West Theater on...
Featured
Islamorada
Florida Keys Farmers Market
-
Spend your Sunday soaking up local flavor at the Florida Keys Farmers Market in Islamorada. Held every Sunday from 10 a.m. to 3 p.m. in the parking...
Featured
Key West
7th Annual BBQ Rib Battle
-
Sunday, September 6, 2026, from 11:30 a.m. to 4 p.m. Come hungry for the 7th Annual BBQ Rib Battle, a lively Key West cookoff bringing grill masters...
Featured
Islamorada
Islander Resort Coastline Cleanup
Give back to the beautiful shores of Islamorada during the Islander Resort Coastline Cleanup, held every Monday in September at 3 p.m. This relaxed...
Featured
Key West
Glow Hours at Hugh’s Views
-
Every Monday and Tuesday, experience Glow Hours at Hugh’s View in Key West, a one-of-a-kind rooftop evening set above The Studios of Key West. Take in...
Featured
Key West
Monday Night Jazz Jams
-
Kick off the week with the smooth sounds of Monday Night Jazz Jams at the William Weech American Legion Post 168 in Key West. Held every Monday from 8...
Featured
Key West
Aqua Idol at the Legion
Every Tuesday from September 8 through October 13, 2026, beginning at 6 p.m. Cheer on local singers while supporting a great cause during Royal Aqua...
Featured
Key West
Hemingway in a Funny Way at Comedy Key West
-
Raise a glass to one of Key West’s most legendary literary figures during this playful tribute to Ernest Hemingway at Comedy Key West. Led by comedian...
Featured
Key West
Arts & Drafts
-
Get creative midweek with Arts & Drafts at The Retro Room in Key West, held every Wednesday from 7 to 9 p.m. This relaxed, social art night pairs a...
