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
Mile 0 Fest
-
Experience Mile 0 Fest in the stunning Florida Keys! Enjoy five days of top Texas Red Dirt & Americana music, beachfront parties, and unforgettable...
Featured
The Lower Keys
Beaver Moon Full Moon Dinner at Little Palm Island
Tuesday, November 24, 2026, by reservation. Dine under the glow of the Beaver Moon at Little Palm Island, the private island resort in the Lower Keys...
Featured
Marathon
Dolphin Research Center’s Dolphin Sunset Celebration
Experience a truly unforgettable evening at Dolphin Research Center in the Florida Keys with the Dolphin Sunset Celebration, an intimate once-a-month...
Featured
Key West
Thanksgiving Sunset Dinner Cruise
Thanksgiving Day 2026, boarding for a 5:00 p.m. departure in Key West. Spend Thanksgiving on the water. Sunset Watersports runs a two-hour...
Featured
Key West
Thanksgiving Feast at Key West Cooking Show
Thursday, November 26, 2026, with seatings at 11 a.m. and 2 p.m. in Key West. Gather your crew and let the Key West Cooking Show take care of the...
Featured
Key West
Thanksgiving at Hot Tin Roof
Thursday, November 26, 2026. Hot Tin Roof serves a four-course prix fixe holiday menu that celebrates cherished traditions, built around refined...
Featured
The Lower Keys
40th Annual Island Art Fair
Hosted by the Lower Keys Chamber of Commerce, the Island Art Festival is a free, family-friendly event celebrating local creativity and community...
Featured
Key West
Black Friday Market: Shopping Extravaganza
Get ready for the ultimate Black Friday shopping experience at the Black Friday Market: Shopping Extravaganza! Join us on Friday, November 28 from 10...
Key West
Writing a Life: The Building Blocks of Memoir with Janice Gary
Wednesday, December 2, 2026, from 2:00 to 4:00 p.m. Janice Gary teaches the building blocks of memoir at The Studios of Key West, a two-hour workshop...
Featured
Key West
It's A Wonderful Live: A Live Radio Play at Waterfront Playhouse
December 3-17, 2026 It’s a Wonderful Life: A Live Radio Play at Waterfront Playhouse brings a festive twist to the holiday season with a creative...
Key West
End of Prohibition Celebration
-
Thursday, December 3 through Saturday, December 5, 2026. Key West spends three days marking the one thing the Constitution has only ever done once...
Key West
Scarlet Soirée: A Holiday Affair
Thursday, December 3, 2026, 7:00 to 11:00 p.m. Island Girl Promotions hosts the Scarlet Soirée, a holiday benefit on the rooftop at Celtic Conch...
Key West
Winter Members’ Exhibit: Let the Light In
-
December 3 through December 31, 2026, daily from 10:00 a.m. to 4:00 p.m. The Studios of Key West hangs its winter members’ exhibition, Let the Light...
Featured
Islamorada
Islamorada Sailfish Tournament
-
December 4–6, 2026 The Islamorada Sailfish Tournament kicks off the Florida Keys Gold Cup Championship as the first leg of the three-tournament series...
Featured
Key West
First Fridays on Fleming
-
Every first Friday of the month from 6 to 9 p.m., Fleming Street in Key West transforms into a lively celebration of island creativity, community, and...
Featured
Key West
Junk in the Trunk: Holiday Re-Gifting Sale
Saturday, December 5, 2026, from 8:00 a.m. to 1:00 p.m. Junk in the Trunk puts a holiday spin on its reuse and repurpose concept with the first of two...
