Quaint New England Villages, frozen snowmen and the scent of wood-burning stoves may be some people’s idea of the holiday season. But not here in the Keys and certainly not in Key West where we celebrate the holidays in true island style.


As one of America’s top tropical holiday destinations, Key West is a small town that’s big on holiday cheer. 


And nothing embraces its holiday spirit more than the annual Holiday Fest celebration which kicks off at 6pm on Wednesday, November 27 in Key West’s Historic Seaport. There will be lots going on that night including a traditional Tree Lighting Ceremony, Classic Auto Show, Pet Pictures with Santa and the Lighting of the Harbor Walk.
Here’s what else is going on:

Friday, December 6
6 – 8pm Holiday Historic Inn Tours – Night 1
Explore some of the most romantically decorated inns on the island, including He-mingway Rum Co. Distillery, Amsterdam’s Curry Mansion Inn, The Weatherstation Inn, The Gardens Hotel, and Island City House Hotel. 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.

6 – 8pm Pet Pictures with Santa
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 7
7pm Key West Hometown Holiday Parade
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.

Monday, December 9 – Sunday, December 22
Conch Tour Train Holiday Lights Tours
Multiple nightly tours begin with cider and cookies, and convey caroling passengers through streets and neighborhoods to revel in the magically illuminated city of Key West.

Friday, December 13
6 – 8pm Holiday Historic Inn Tours – Night 2
Explore some of the most romantically decorated inns on the island, including the Avalon Bed & Breakfast, Wicker Guesthouse, The Mermaid & the Alligator, Santa Maria Suites Resort, Key West Butterfly and Nature Conservatory. Arrive at each property via free trolley or your own transportation and explore its unique architec-ture, history and holiday ambiance while tasting sweet and savory holiday treats and libation samplings.

Saturday, December 14
10am – 2pm Annual Parade of Paws & Holiday Bazaar
Costumes encouraged! Takes place at Higgs Beach / Higgs Dog Park Check-in at 9:00am. Benefits the Florida Keys SPCA.

8pm Schooner Wharf 29th Annual Key West Lighted Boat Parade
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 18
5 – 9pm 4th Annual Holiday Concert & Bazaar
This festive free party features Key West’s finest artisans, musicians and choirs, a-long with a spectacular holiday light show. Takes place at the Custom House Museum.

Sunday, December 22
5pm Lighting of the Menorah
A heartfelt ceremony at Bayview Park.

Tuesday, December 31
Noon Annual Key West Dachshund Walk
Dachshund’s and Dachshund impersonators along with their human companions ga-ther at Fleming and Whitehead Streets before parading through downtown streets lined with adoring fans.

New Year’s Eve Celebrations
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.

But that’s just the half of it. For a complete schedule of holiday happenings, ticket info and room bookings, go to keywestholidayfest.com or call 305-296-4959.

Happy Holidays!