See all Key West Christmas happenings this year!
Key West welcomes Christmas 2025 in the historic downtown and Mallory Square, where island lights and festive performances blend tropical charm with holiday cheer. Winter festivals, Santa visits and festive performances include waterfront concerts, artisan markets and spirited parades that make the season unforgettable.
Find the best Key West Christmas happenings this year!
Key West Christmas Events
Key West Christmas Markets and Shopping
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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 talented ensembles, and be captivated by a magical animated holiday projection show on the museum's facade. Indulge in festive food and libations while exploring the charming Festival of Trees, decorated by local students.
Key West Christmas Movies, Theater and Entertainment
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Experience the magic of cinema under the stars with Tropic Cinema's 'Movies Under the Stars' series. This free outdoor screening features the beloved holiday film 'Elf'. Join them on Eaton Street for a cozy evening with concessions available inside the Tropic lobby. Bring your own chairs or blankets for a comfortable viewing experience.
Key West Other Christmas Activities
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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 memories.
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