Key West Christmas Events & Things to Do 2025

Experience the magic of Key West during the holidays with the Conch Tour Train's annual Holiday Sights and Festive Nights Tour. This enchanting 1-hour journey takes you through the island's most elaborately decorated neighborhoods, showcasing stunning displays of festive lights on houses and businesses. Special holiday lights glasses are included...

Experience the festive spirit of Key West as homeowners compete in the annual holiday lights contest. Residents and visitors alike can cast their votes for the most dazzling displays, with cash prizes awarded to the top three decorated homes. It's a wonderful opportunity to see the island sparkle with holiday...

Experience the magic of the holidays in Key West with Old Town Trolley's Festive Nights Tour. Locals go all out decorating their historic homes in a dazzling display of lights and creative touches for a friendly competition. This narrated 60-minute tour offers a unique way to enjoy the island's festive...

Key West transforms into a festive wonderland during the holiday season, offering a warm escape from the cold. Visitors can enjoy a variety of events from late November through December, including illuminated light displays along the Historic Seaport, unique artisan markets perfect for holiday shopping, and lively parades. Experience cultural...

Experience the festive spirit at the Annual Holiday Concert & Bazaar, hosted by the Key West Art & Historical Society. This popular celebration transforms the historic porch and street in front of the Custom House into a vibrant marketplace. Discover unique handcrafted gifts from local artisans, enjoy live music from...

Celebrate Christmas in Key West with the Ultimate Adventure H2.0! This 3.5-hour catamaran excursion offers a thrilling blend of activities, including parasailing, jet skiing, a banana boat ride, and access to Florida's only certified ocean waterpark. It's the perfect way to experience Key West's aqua-blue waters and create unforgettable holiday...