Instead of anticipating holidays filled with shivery winter chill, imagine indulging in a December getaway to balmy Key West. That’s right — a sun-splashed holiday season, alive with warmth and cheer, is on tap in the subtropical island city. The weeks leading up to Dec. 25 are sprinkled with only-in-Key-West events and plenty of reasons to (wait for it) “don your gay apparel.”
Explore some of the cheeriest seasonal celebrations here.
Key West’s lovely “Mermaid and Alligator” inn is shown here decorated for a past holiday season.
Nov. 23: Lighting of the Key West “Harbor Walk of Lights.” The eagerly awaited pre-Thanksgiving event takes place at 6 p.m. at Greene and Elizabeth streets, with the lighting of a quirky holiday tree featuring plastic foam trap floats, a nautically decorated pine Christmas tree and a creatively-crafted lobster trap tree along the Key West Historic Seaport’s Harbor Walk. Best of all, the Harbor Walk is lit nightly through New Year’s Eve.
Dec. 2-3, 9-10 and 16-17: Hot Pink Holidays. Three merry LGBT weekends, sponsored by the renowned Key West Business Guild, are full of festive activities as well as special retail opportunities on the island. Events include a Conch Train holiday lights tour and caroling. Holiday revelers can even celebrate with “Sandy Claws” at happy hours.
Dec. 3: Key West City Hometown Holiday Parade. This is not your mama’s holiday parade — it blends traditional charm with an offbeat Key West flair. Local flavor prevails with marching bands, motorized and non-motorized floats, eccentric “elves,” and lively community participation. The route begins at the island’s Bayview Park, and the best viewing spots are along Duval Street and Truman Avenue.
Enjoying the magnificent ballet “Nutcracker Key West” is a holiday tradition in the island city. (Photo by Peter Arnow)
Dec. 9 and 16: Holiday Historic Inn Tours. Two evenings of tours include trolley transportation between several participating inns, all wonderfully decorated for the holidays. As well as exploring the gorgeous properties, attendees can enjoy treats and libations at each stop. Tickets are $30 per person (a bargain for the lovely event that’s a favorite of savvy locals).
Dec. 10: Parade of Paws and Holiday Bazaar. What would the holidays be without furry family members? In Key West, they get a seasonal soiree of their own — the annual pet parade at Higgs Beach Dog Park. Whether you’re watching or taking part, it’s a tail-wagging joy. To participate, pets’ humans gather funding pledges from family and friends, and top earners win bragging rights for titles of the 2016 Parade of Paws king, queen, prince, princess, duke or duchess for their treasured companions. Pets and people can also take photos with Santa, enjoy entertainment, food and crafts, and mingle with other holiday-lovers.
Dec. 10: Schooner Wharf Bar Lighted Boat Parade. Imaginatively lighted and decorated vessels, ranging from spunky little rowboats to majestic tall ships, proceed around Key West’s Historic Seaport and harbor areas. The fun begins at 8 p.m., and holiday revelers can watch and applaud from bars, restaurants and resorts in and around the Historic Seaport.
Majestic vessels promenade around Key West Harbor during the annual Schooner Wharf Bar Lighted Boat Parade. (Photo by Carol Tedesco, Florida Keys News Bureau)
Dec. 10-18: Nutcracker Key West. This unique subtropical version of the classic ballet “The Nutcracker” is flavored with characters and sets depicting Key West’s colorful history, vibrant coral reef environment and even free-roaming roosters. Fifteen professional dancers from around the world — including Nurlan Abougaliev, formerly with the Russian National Ballet — join 50 Florida Keys residents to infuse the magical story with Keys imagery. Performances take place at the Tennessee Williams Theatre.
Dec. 21: Custom House Holiday Concert & Bazaar. The Key West Art & Historical Society hosts the inaugural celebration at the historic (and breathtakingly restored) Custom House Museum. Highlights of the evening include performances by musicians and choirs, local artisans showcasing their wares, a light show and even “selfies” with Santa.
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