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  • Some Enchanted Evening

    Waterfront Playhouse 407 Wall St, Key West, FL, United States

    A stunning revue of Rodgers & Hammerstein’s most treasured songs, this elegant theatrical presentation brings five performers into a world of timeless music — from backstage intimacy to full-stage splendor....

    $70

  • 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

  • 20th Annual Pet Pictures with Santa

    Key West Bight Marina 201 William Street, Key West, FL, United States

    Hosted by All Animal Clinic Professional photos by Rob O’Neal LOCATION: At the 16’ Nautical Christmas Tree on the Harbor Walk of Lights at William St. Santa pics with pets...

    $25

  • An Evening with Norman Van Aken

    Key West Cooking Show 291 Front Street, Key West, FL, United States

    Join the Key West Cooking Show for an Evening with Chef Norman Van Aken. A legend in the Key West culinary scene, Van Aken is a James Beard Award winner...

    $140

  • European Style Holiday Market at the Hellings Curry Museum

    Hellings Curry Museum 319 Duval Street, Key West, FL, United States

    Join us on Saturday, December 6th at noon for the Key West Woman’s Club’s first-ever European Style Holiday Market, a festive community event created entirely by our own talented members....

    Free

  • 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