December in the Florida Keys is a magical time filled with festive celebrations, unique island traditions, and plenty of sunshine. Whether you're a local looking for holiday fun or a visitor escaping the winter chill, there's no shortage of events to enjoy in this tropical paradise. From holiday parades and lighted boat displays to live music and food festivals, the Florida Keys come alive with the spirit of the season. At ShineGroup , we're your trusted real estate experts in Key West, dedicated to keeping you informed on all the best things to see and do in our vibrant community. Explore our comprehensive December events calendar and make the most of your time in the Keys! December 1: Southard Street Stroll Key West Artisan Market: Rock the Red Ribbon Edition Sunset Watersports: Thanksgiving Week Specials Key West End of Prohibition Celebration December 4: Comedy Key West: Brendan Eyre Nutcracker Key West December 6 First Fridays On Fleming Coffee Butler Amphitheater: Holiday Village & BeLighted Bike Ride December 7 Key West Holiday Parade Key West Theater: The Kingston Trio December 8 Key West Artisan Market at Southernmost Beach Resort December 9 Old Town Trolley: Holiday Nights Tours December 10 LaTeDa Christmas Party Fringe Theater: Tony Konrath's A Christmas Carol December 11 Gay Key West Holiday Lights Trolley Tour December 12 Red Barn Theatre: The Foreigner December 13 Stock Island Lighted Boat Parade Waterfront Winter Wonderland Key West Art & Historical Society: Holiday Concert & Bazaar Pigeon Key Holiday Spectacular December 14 Schooner Wharf Bar Lighted Boat Parade December 15 Key West Artisan Market: Fill the Pantry Edition Holiday Full Moon Sail December 18 Fringe Theater's Holiday Train Ride Key West Art & Historical Society Historic Seaport Sail: Plant a Million Corals Project Comedy Key West: Jim Florentine Cocoa and Carols Holiday Sails December 19 Walk on White Third Thursday Art Walk December 22 Key West Artisan Market: Shop Local Edition December 24 Christmas Celebration Sunset Sails December 25 Christmas Day Brunch Sail December 31 New Year's Eve Conch Shell Drop at Sloppy Joe's New Year's Eve Gatsby Gala at First Flight Island Restaurant & Brewery Schooner Wharf Bar: New Year's Eve Lowering of the Pirate Wench New Year's Eve Red Shoe Drop New Year’s Eve Dockside Party