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 22 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 22 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.

Friday, December 1, 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.

Saturday, December 2, 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 (of both the clawed AND Santa Claus’d kind).

Wednesday, December 6, Wesley House Family Services Key West Lighted Bike Ride, registration/check-in 6:00pm at Bayview Park: It’s a festive, costumed peddling party toy drive which launches from the Park at 7:00 p.m. Registration is one unwrapped new toy.

Wednesday, December 6 through Saturday, 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 8, Holiday Historic Inn Tours – Night 1, 6:00pm-8:00pm: Explore some of the most romantically decorated inns on the island, including La Te Da Hotel, Wicker Guesthouse, Weatherstation Inn and Southwinds Motel. 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 9, The 4th 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 9, the 27th 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.

Friday, December 15, Holiday Historic Inn Tours – Night 2, 6:00pm-8:00pm: Explore some of the most romantically decorated inns on the island – the Avalon Bed & Breakfast Hotel, The Mermaid & the Alligator, The Gardens Hotel, Island City House Hotel and the Key West Butterfly and Nature Conservatory. 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.

Wednesday, December 21, 2nd 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.

Sunday, December 31, the 12th 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.

Sunday, 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.  “But with so many events, it can be difficult for locals and visitors to stay on top of what’s happening and when. The Lodging Association makes planning super easy by providing our one-stop online information resource at keywestholidayfest.com.”

Key West Holiday Fest is presented by the Margaritaville Key West Resort & Marina, The Ocean Key Resort & Spa, Historic Tours of America, 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.