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  • Santa at the Shops of Mallory Square

    Shops at Mallory Square 291 Front Street, Key West, FL, United States

    Ho ho ho! Bring the family for a festive Key West holiday moment with Santa himself at The Shops at Mallory Square. Enjoy photos, holiday cheer, and a little island...

    Free

  • Key West City “Hometown Holiday Parade”

    Various Key West, FL, United States

    Parade starts on Truman Ave. (at White St.) then proceeds to Duval St., then down Duval St. ending at Eaton St. The most charming hometown parade you’ll ever see with...

    Free

  • Glow Hours at Hugh’s Views

    Glow Hours at Hugh’s Views
    The Studios of Key West 533 Eaton Street, Key West, FL, United States

    Our Hugh’s View roof terrace offers the best views in town, and an ideal spot to catch the sunset and a drink with friends. The bar is open, admission is...

    Free

  • Old Town Trolley’s Holiday Sights and Festive Nights Tour

    Mallory Square Key West, FL, United States

    No need to gas-up the snowblower this year if you’re planning a holiday escape to the Conch Republic! Here, ‘Christmas chill’ means rockin’ your flops and kicking back island-style and...

    $24.53 – $36.28

  • Glow Hours at Hugh’s Views

    Glow Hours at Hugh’s Views
    The Studios of Key West 533 Eaton Street, Key West, FL, United States

    Our Hugh’s View roof terrace offers the best views in town, and an ideal spot to catch the sunset and a drink with friends. The bar is open, admission is...

    Free

  • Truman Waterfront Farmers Market

    Truman Waterfront Farmers Market
    Truman Waterfront Park Southard Street, Key West, FL, United States

    Join us every Thursday from 2 pm to 7 pm at the Truman Waterfront for fresh produce grown in Homestead, gorgeous orchids & native plants, artisan selection of meats and...

    Free

  • Holiday Historic Inn Tour

    Various Key West, FL, United States

    Join us for an enchanted evening of decorated historic inns while enjoying light sweet or savory holiday treats and holiday cheer at each property. Visit each property, explore the unique...

    $43.93

  • The Great Gingerbread Build

    Harry S. Truman Little White House 111 Front Street, FL, United States

    Come one, come all to the Great Gingerbread Build at the Harry S. Truman Little White House. This event is free and open to the public. We will have gingerbread...

    Free

  • The Nightmare Before Christmas presented by the Key West Film Society

    Tropic Cinema 416 Eaton Street, Key West, FL, United States

    Movies Under the Stars Kick off the holiday season with a magical night under the stars! In Tim Burton’s beloved stop-motion classic The Nightmare Before Christmas, Jack Skellington—the Pumpkin King...

    Free