Key West Events Calendar

From annual festivals to holiday celebrations, the fun never stops in Key West. We're looking forward to these upcoming Key West events. For details on any event or planning a holiday vacation, contact our local team! We're happy to provide nearby vacation rental recommendations and the inside scoop on all things Key West. 

key west headdress ball

FANTASY FEST: KEY WEST HEADDRESS BALL

Oct 24 2024 - 6:30pm
October 24 Key West FANTASY FEST: KEY WEST HEADDRESS BALL WEBSITE Talented headdress makers compete for first- through third-place prizes. The premiere LGBTQ event of the Fantasy Fest Celebration, this popular event returns to the Coffee Butler Amphitheater in Truman Waterfront Park. Doors open to...Read more
Upcoming Events
fantasy fest 2024

Fantasy Fest Key West 2024

Oct 18 2024 - 8:00am to Oct 27 2024 - 5:00pm
Started in 1979 by Key West Locals, this 10-day parade has turned into one of the best and biggest parties Key West has to offer!Read more
Festivals
race world key west

Raceworld Offshore World Championships

Nov 3 2024 - 10:00am to Nov 10 2024 - 11:00pm
November 03 - 10, 2024 Key West RACE WORLD OFFSHORE WORLD CHAMPIONSHIP WEBSITE Leading American and international powerboat teams compete in high-speed races in the powerboat range World Championship. On race days, spectators can get an unmatched view from areas at the Truman Waterfront Race...Read more
Upcoming Events
key west film festival

Key West Film Festival

Nov 13 2024 - 10:00am to Nov 17 2024 - 11:00pm
November 13 - 17, 2024 Key West KEY WEST FILM FESTIVAL WEBSITE Named one of the top 25 coolest film fests in the world by Moviemaker magazine, the 13th annual Key West Film Festival is set for Nov. 20-24.Read more
Festivals
key west lighting

Lighting of the Key West Harbor Walk of Lights

Nov 27 2024 - 5:00pm
November 27 Key West Lighting of the Key West Harbor Walk of Lights Gather on the Harbor Walk plaza at Greene and Elizabeth St. to best see the official lighting of the 2024 Key West Harbor Walk of Lights with lights and creative displays reflecting...Read more
Holiday Events

Key West Holiday Parade

Dec 7 2024 - 7:00pm
December 07 Key West Key West Holiday Parade Website Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks off...Read more
Holiday Events
key west lighted boat parade

Schooner Wharf Bar Lighted Boat Parade

Dec 14 2024 - 8:00pm
December 14 Key West Schooner Wharf Bar Lighted Boat Parade Website Don't miss this magical nautical display of holiday lights on board every manner of watercraft in Key West Harbor. The judges stand is located at Schooner Wharf, 202 William St. Viewing is available from...Read more
Holiday Events

Key West Triathlon

Dec 15 2024 - 7:30am
December 15 Key West Key West Triathlon Website The Key West Triathlon begins and ends at College of the Florida Keys, 5901 College Rd., shifting from the traditional location because of ongoing construction along S. Roosevelt Avenue. All fitness levels are welcomed. Races include the...Read more
Holiday Events
Nutcracker

Nutcracker Key West

Dec 5 2024 - 7:30pm to Dec 15 2024 - 7:30pm
December 05 - 15, 2024 Key West Nutcracker Key West Website Performed every other year, Nutcracker Key West is a sumptuous, artful theatrical experience wrapped as a perfect holiday gift for the Southernmost City, returning December 2024. The Key West production comes complete with chickens,...Read more
Holiday Events

Old Town Trolley: Holiday Nights Tours

Dec 9 2024 - 7:45pm to Dec 23 2024 - 7:45pm
December 09 - 23, 2024 Key West Old Town Trolley: Holiday Nights Tours Website Take the trolley for a tour of the Key West residential neighborhoods known for going all-out with holiday home decorations. Make this your new holiday tradition with friends and family. Narrated...Read more
Holiday Events

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