Visions of winter holiday delights traditionally involve frosty white landscapes and warm crackling fires, but few U.S. destinations can boast a solid month of festivities and holiday merry-making to compare with the annual Key West Holiday Fest. The island-wide Keys-centric celebration kicked off on Wednesday, November 21 with the lighting of the Key West Harbor “Walk of Lights” and continues through December 31, with highlights including (but not limited to):
Wednesday, November 21 through New Year’s Eve: Key West Harbor Walk of Lights at the Historic Seaport: Revel in a wonderland of light-bedecked palm trees, Christmas trees, ships, shops, restaurants and watering holes, dazzlingly decorated for the holiday season from Lazy Way Lane at the Green Street Plaza to the Ferry Terminal at Grinnell Street.
Sunday, December 2: Lighting of the Menorah, 5:00pm at Bayview Park.
Sunday, December 2: “Messiah” concert, 7:00pm at Key West United Methodist Church.
Wednesday, December 5: Wesley House Family Services Key West Lighted Bike Ride: It’s a festive, costumed peddling party toy drive which launches from Bayview Park at 7:00 p.m. Registration/check-in 6:00pm; registration is one unwrapped new toy.
Thursday, December 6 through Sunday, December 23: Old Town Trolley Holiday Lights & Sights Tours and Conch Tour Train Holiday Lights Tours:Multiple nightly tours convey caroling passengers through streets and neighborhoods to revel in the magically illuminated city of Key West.
Friday, December 7, Holiday Historic Inn Tours – Night 1, 6:00pm-8:00pm: Explore some of the most romantically decorated inns on the island, including The Gardens Hotel, Island City House Hotel, Amsterdam’s Curry Mansion Inn, The Weather Station Inn, and Key West Butterfly and Nature Conservancy. Arrive at each property via free trolley or your own transportation and explore its unique architecture, history and holiday ambiance while tasting sweet and savory holiday treats and libation samplings.
Friday, December 7, Pet Pictures with Santa, 6:00pm-8:00pm: Pack up Fifi and Fido and delight in Pet Pictures with Santa at the Christmas tree at the foot of William Street at the Key West Bight Marina. Proceeds benefit the Boys & Girls Club of the Keys.
Friday, December 7-Dec. 16, Nutcracker Key West: There’s only one place in the world where you can experience the spectacularly crafted Nutcracker Key West ballet, inspired by the unique and colorful environment of the Florida Keys, with snowy egrets on shimmering salt ponds, a wicked Rooster-King, an exquisite Sea Star Fairy and “underwater sequences of almost unimaginable beauty.
Saturday, December 8, Key West Hometown Holiday Parade, 7:00pm: Hundreds of spectators line the streets for the homegrown parade which kicks off at Bayview Park and travels along Truman Ave and Duval Streets with festooned floats and marching groups consisting of adults, children, and elves, along with assorted hoofed and whiskered friends.
Friday, December 14, Holiday Historic Inn Tours – Night 2, 6:00pm-8:00pm: Explore some of the most romantically decorated inns on the island, including the Hemingway Rum Company Distillery, Old Town Manor, Wicker Guesthouse, The Mermaid & The Alligator, Suite Dreams Inn, and Santa Maria Suites Resort. Arrive at each property via free trolley or your own transportation and explore its unique architecture, history and holiday ambiance while tasting sweet and savory holiday treats and libation samplings.
Saturday, December 15, Annual Parade of Paws & Holiday Bazaar at Higgs Dog park, 10:00am-2:00pm (9:00am check-in): – Benefits the Florida Keys SPCA. Costumes encouraged!
Saturday, December 15, the 28th annual Schooner Wharf Lighted Boat Parade, 8pm: A glittering parade of illuminated watercraft. Arrive at the Key West Bight Marina at the Historic Seaport early in order to stroll through the magical Key West Harbor Walk of Lights with its array of shops, restaurants and watering holes, charmingly decorated for the holidays.
Wednesday, December 19, 3rd Annual Holiday Concert & Bazaar at Custom House Museum, 5:00pm-9:00pm: This festive free party features Key West’s finest artisans, musicians and choirs, along with a spectacular holiday light show.
Monday, December 31, Annual Key West Dachshund Walk, 12:00 noon: Dachshund’s and Dachshund impersonators along with their human companions gather at Fleming and Whitehead Streets before parading through downtown streets lined with adoring fans.
Monday, December 31: For your midnight toast, chose between an abundance of uniquely Key West New Year’s Eve Celebrations, including the Conch Shell Drop at Sloppy Joe’s Bar on Duval Street; the world-famous Red High Heel Drop with Sushi the Drag Queen at the Bourbon St. Pub; the saucy Pirate Wench Drop at the Historic Seaport and the Key Lime Wedge in a Margarita Glass drop at the Ocean Key Resort.
“The winter holidays are a wonder-filled time to experience a very special type of Key West magic,” commented Jodi Weinhofer, President of the Lodging Association of the Florida Keys and Key West. “The Lodging Association has made planning super easy by providing a one-stop online holiday festivity information resource at keywestholidayfest.com, so be sure to visit our site for more information on these events and many more.”
Key West Holiday Fest is presented by First State Bank, Historic Tours of America, Margaritaville Key West Resort & Marina, Ocean Key Resort, The Lodging Association of the Florida Keys and Key West, and the Monroe County Tourist Development Council. For more information, contact the Lodging Association at 305-296-4959 or visit keywestholidayfest.com.