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
Morada Way Third Thursday Art Walk
Dates: Every Third Thursday of each month from 6 to 9 p.m., experience the vibrant Morada Way Arts & Cultural District Art Walk in Islamorada! Enjoy...
First Fridays on Fleming
Every First Friday (6–9pm), Fleming Street in Key West comes alive for First Fridays on Fleming — a monthly evening of local shopping, gallery...
Burgers & Buffet Tunes: A Tribute Show at Comedy Key West
There are many places to eat lunch in Key West. But there’s only ONE place to have lunch with a legend. Join us for Key West’s only all-inclusive dine...
Hemingway in a Funny Way at Comedy Key West
Comedy Key West is happy to be bringing back the first show paying tribute to the funny side of the life and works of Ernest Hemingway. A few blocks...
Open Air Market at Boondocks
Explore Boondocks Open-Air Market every Saturday 9 AM to 2 PM at Mile Marker 27.5 on Ramrod Key. Discover 20+ local vendors offering handcrafted...
Glow Hours at Hugh’s Views
Every Monday & Tuesday Experience Glow Hours at Hugh’s View in Key West! Enjoy breathtaking sunset views, vibrant art installations, and live music...
Walk on White
Walk on White, one of Key West’s most popular monthly art strolls, kicks off its 2025/2026 season on October 16 and continues monthly on every third...
Key West Farmers Market
Discover the vibrant Florida Keys Farmers Market! Enjoy fresh local produce, unique artisan goods, delicious food, live music, and a welcoming island...
Monday Night Jazz Jams
Mondays, 8:30 – 11:30 p.m. William Weech American Legion Post 168 803 Emma St., Key West Start your week with live music at Monday Night Jazz Jams at...
A ROCK SAILS BY at Red Barn Theater
Mar 31 - Apr 25, 2026 Shows: Tuesdays-Saturdays at 7:30pm When a UFO is sighted heading towards Earth, astrophysicist Dr. Lynn Cummings grants an...
Sea Level Rise, Past and Future – So Long and Thanks for All the Fish
Explore the evolving story of Key West through an engaging talk on sea level rise and its lasting impact on the island’s landscape and history. Led by...
Jessimae Peluso at Comedy Key West
April 1, 2, 3, and 4, 2026 | 8:00 PM Comedy Key West welcomes back Jessimae Peluso for four nights of bold, high-energy stand-up this April. A...
RAMS HEAD PRESENTS: SQUIRREL NUT ZIPPERS
The Squirrel Nut Zippers celebrate the 30th anniversary of their platinum-selling album Hot! For this special show, the Zippers will perform Hot in...
Habitat’s Tropical Gala at Truman Little White House
Enjoy an evening of celebration, community, and impact at Habitat for Humanity’s Tropical Gala in Key West. Held at 111 Front Street, this lively...
Spanish Fly Shark Tournament (2026)
Experience the thrill of the Key West Shark Tournament in the beautiful Florida Keys! Join fellow anglers for exciting shark fishing, cash prizes, and...