Calendar of Events
Sep24Haunted Tours
Explore the SPOOKY side of Key West with a haunted historical tour.
Date: May 14, 2026 - December 31, 2026
Time: Thursday evenings (varies by operator)
Location: Off-Site (Key West – walking or trolley tour)
Sep24Key West Farmers Market
Visit the Key West Farmers Market every Thursday at the Truman Waterfront.
Date: May 14, 2026 - December 31, 2026
Time: Thursday's, 2:00 pm – 7:00 pm
Location: Truman Waterfront
Sep26Sunset Sails
There is nothing quite like a Key West sunset, and the second-best place to view one (after the Sunset Pier, of course) is out on the water.
Date: May 9, 2026 - December 31, 2026
Time: Saturday's, Varies (sunset)
Location: Off-Site (Key West waters)
Sep27World Class Fishing
The Florida Keys are known for amazing fishing. From the flats and shallows, sight fishing for permit, tarpon or bonefish or in the deeper waters of the backcountry, on the hunt for snapper, grouper or tuna.
Date: May 10, 2026 - December 31, 2026
Time: Sunday's, Varies by charter
Location: Off-Site (Florida Keys waters)
Oct16Fantasy Fest
Fantasy Fest turns Key West into a spectacle of masked processions, parties, contests and dances attended by tens of thousands.
Date: October 16 -25, 2026
Time: Varies by event
Location: Key West (multiple venues)
Nov01Race World Offshore Championships
Experience the most powerful of water activities in Key West with the Race World Offshore World Championships.
Date: November 1 - 8, 2026
Time: Daytime (race schedule varies)
Location: Key West (Gulf side – six-mile course)
Nov26Thanksgiving Dinner at Café Marquesa
Gather together in the heart of Old Town for an exquisite Thanksgiving evening.
Date: November 26, 2026
Time: By Reservation
Location: Café Marquesa
Dec24Christmas Eve and Christmas Day Dinner
Celebrate the joy of the holiday with a festive four-course prix fixe menu.
Date: December 24 – 25, 2026
Time: By Reservation
Location: Café Marquesa
Jan26Mile 0 Fest
Experience the “friendliest festival” in paradise, featuring the best Red Dirt and Americana music at island venues, including Sunset Pier.
Date: January 26, 2027 - January 30, 2027
Time: All day
Location: Key West (multiple venues)
Apr28Key West Songwriter Festival
Discover the stories behind the songs at the world’s largest songwriters festival, featuring five days of live music, including shows at Sunset Pier.
Date: April 28, 2027 - May 2, 2027
Time: All Day
Location: Key West (multiple venues)
