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.
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Islamorada
Morada Way Third Thursday Art Walk
Nov 20, 2025, Dec 18, 2025, Jan 15, 2026, Feb 20, 2026, Mar 19, 2026, Apr 16, 2026, May 21, 2026, Jun 18, 2026, Jul 16, 2026, Aug 21, 2026, Sep 17, 2026, Oct 15, 2026
Dates: Third Thursday of each month from 6 to 9pm Experience the vibrant Morada Way Arts & Cultural District Art Walk in the Florida Keys! Enjoy local...
Islamorada
Islamorada Fishing Club Captain's Cup Sailfish Tournament
Jan 20 - 21, 2026
Presented by the Islamorada Fishing Club, the event is the second leg of the three-pronged Florida Keys Gold Cup Sailfish Championship trifecta...
Islamorada
Dive Into Art: Stories from the Sea at History of Diving Museum
Jan 21, 2026
Join the History of Diving Museum for Immerse Yourself!, a free monthly lecture series held at 7 PM on the third Wednesday of every month. Each...
Islamorada
Cheeca Lodge & Spa Presidential Sailfish Tournament
Jan 23 - 25, 2026
The Cheeca Lodge Presidential Sailfish Tournament takes place January 23rd through 25th in Islamorada and serves as the final leg of the three...
Islamorada
Island Boat Show 2026
Jan 23 - 25, 2026
Experience the Island Boat Show in the beautiful Florida Keys! Explore top boat brands, enjoy waterfront views, live music, delicious food, and family...
Islamorada
History of Diving Museum Guided Tours
Jan 24, 2026
Explore the History of Diving Museum in Islamorada — an immersive, family-friendly dive into underwater exploration. View vintage gear, rare artifacts...
Islamorada
Islamorada Women's Sailfish Tournament IWST (2026)
Jan 30 - Feb 1, 2026
This light-tackle challenge celebrates its 40th year along with its new affiliation with the Ladies, Let’s Go Fishing organization. Instruction on how...
Islamorada
Swamp Guides Ball
Jan 30 - 31, 2026
In this annual all-release competition organized by the Florida Keys Fishing Guides Association, anglers target bonefish, redfish and snook. The...
Islamorada
Islamorada Bartenders Sailfish Open
Feb 1 - 2, 2026
Headquartered at the Lorelei Restaurant & Cabana Bar, this fun fishing event is open to actively employed Keys bartenders and restaurant employees...
Islamorada
Poor Girls Sailfish Tournament
Feb 3 - 4, 2026
Women anglers vie for trophies awarded to the first-, second- and third-place teams, grand champion and runner-up grand champion anglers, as well as...
Islamorada
Beats on the Bay - Touch & Go at Founders Park
Feb 6, 2026
Experience Beats on the Bay in the Florida Keys! Enjoy live music, delicious food, and stunning waterfront views at this vibrant event. Perfect for...
Islamorada
Dive Into Art and Music at The Florida Keys Brewing Co.
Feb 6, 2026
Experience an evening of live music, art, and good vibes at Florida Keys Brewing Co in Islamorada! This benefit event, presented by the History of...
Islamorada
CONNECTIONS PROJECT Pop-Up, Islamorada Chamber After Hours at The Islander
Feb 17, 2026
Join The Connections Project: A Mosaic of the Keys— pop-up event across the Florida Keys celebrating local visual and performing artists. Explore...
Islamorada
Gigantic Nautical Market
Feb 21 - 22, 2026
Experience the Upper Keys Rotary Gigantic Nautical Market in Islamorada (Founders Park, MM 87) Feb 21–22, 2026 — a seaside outdoor boat show, gigantic...
