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
Key West History Through Five Craft Cocktails
-
Available October 20–24 and October 27–31, 2026, from 5 to 7 p.m. Raise a glass to Key West’s colorful past during Key West History Through Craft...
Featured
Key West
Hedwig and the Angry Inch at Waterfront Playhouse
October 15-23, 2026 Hedwig and the Angry Inch opens Waterfront Playhouse’s 88th season with a bold and electrifying rock musical experience presented...
Featured
Key West
Burgers & Buffet Tunes: A Tribute Show at Comedy Key West
-
There are plenty of places to enjoy lunch in Key West, but only one invites you to dine with a legend. Burgers & Buffett Tunes at Comedy Key West is a...
Featured
Marathon
MCT Children's Summer Theatre Presents Dare to Dream Jr.
-
July 10–11, 2025 – 7:00 p.m. July 12, 2025 – 3:00 p.m. Young performers from Marathon Community Theatre step into the spotlight for Disney’s Dare to...
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...
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
Key West Farmers Market
-
Discover the vibrant Florida Keys Farmers Market, where fresh local flavors, handmade treasures, and island charm come together in a lively open-air...
Featured
Key West
Photography Masterclass with Frank Stewart
Friday, October 23, 2026, from 1 to 3:30 p.m. Photographers can receive in-depth feedback on their work during a Portfolio Review with acclaimed...
Key West
Southernmost Playboy House - Beach Bunny Pool Party Bash
Friday, October 23, 2026, from 10:30 a.m. to 5:00 p.m. The Southernmost House throws an oceanfront, adults only pool party during Fantasy Fest, billed...
Featured
Islamorada
Treasure Treat Night
Available on select dates October 20–24 and October 27–31, 2026. Mix, shake, and sip your way through the world of rum during Rum Revelations: A...
Featured
Key West
Screaming Green Halloween
Saturday, October 24, 2026, from 10 a.m. to 2 p.m. Celebrate Halloween with a green twist during Screaming Green Halloween at the Key West Tropical...
Key Largo
MarineLab's Haunted Lagoon
Saturday, October 24, 2026 from 6:00 to 8:30 PM. We dare you to snorkel MarineLab's Haunted Lagoon. Spooky science, ghoulish games and terrifying...
Islamorada
8th Annual Trunk or Treat Halloween Party
Saturday, October 24, 2026, from 6:00 to 8:30 p.m. The Village of Islamorada throws its 8th Annual Trunk or Treat Halloween Party on the Great Lawn at...
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...
