Spend the holiday season with friends and family exploring all that Key West has to offer! Monroe County residents can enjoy the Old Town Trolley tour for FREE when accompanied by a full fare adult paid guest with Hometown Pass.
The Wesley House Holiday Village is a family-friendly affair boasting an array of delights including Santa photos, engaging community booths filled with games and crafts for the kids, delicious food stalls, live music, and much more! At 8 pm, join the other riders on their route down the iconic Duval Street. It’s an evening of festive cheer you won’t want to miss!
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8:00 PM - 9:00 PM
BeLighted Bike Ride
Join the bikes that have decked the other halls with a ride down the iconic Duval Street. It’s an evening of festive cheer you won’t want to miss!
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7:00 PM - 9:00 PM
Key West Holiday Parade
Experience the ultimate holiday charm at the annual parade in the southernmost city of the continental U.S that delights locals and visitors alike. Kicking off at 7pm, the Holiday Parade features a variety of floats and local groups as they parade down White and Duval.
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5:00 PM - 9:00 PM
Key West Art & Historical Society: Annual Holiday Concert & Bazaar
Customs House
This popular holiday celebration offers a variety of mouthwatering food vendors, unique artisanal booths, and tons of local music. One of the evening’s highlights is the yearly holiday light show designed by Key West High School’s Conch 5 Studios that is projected onto the Customs House.
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Key West Waterfront Winter Wonderland
Coffee Butler Amphitheater
This December, the Coffee Butler Amphitheater at Truman Waterfront Park transforms into a Key West Winter Wonderland, a magical holiday extravaganza for all ages! Experience the charm with an ice-skating rink, thrilling games, rides, enchanting attractions, musical delights, dazzling light displays, and much more. Explore the vendor village filled with delectable food choices and unique creations from local artisans, making it the ultimate destination for festive fun and holiday shopping!
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6:00 PM - 8:00 PM
Key West Lighted Boat Parade
Key West Bight and Harbor, 202 William St.
Get ready for Key West’s 32nd Annual Schooner Wharf Bar Lighted Boat Parade! The excitement starts at 6:00 pm along the Harbor Walk with vibrant decorations and a local steel band playing lively calypso Christmas carols, setting the scene for a festive Caribbean-style celebration filled with infectious rhythms and holiday cheer.
