Key West Holiday Fest

Key West Holiday Fest
The Keys’ Southernmost Celebration

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 which celebrates 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 6 pm on Wednesday, November 21 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. On Saturday, December 8 at 7 pm, the City stages its annual family-friendly hometown Holiday Parade followed by an array of other festive events throughout the month including art walks, decorated trolley rides, special concerts, and more. Highlights include Schooner Wharf Bar’s annual Tree Trimming Party which takes place at 5 pm on Sunday, December 2nd and is also a fundraiser for “Toys For Tots” and “Angels Just For Kids.” Bring your own nautical ornament and enjoy a free holiday cocktail.

Nutcracker Key West – a fabulous island interpretation of the original holiday extravaganza opens on Friday, December 7 and plays through Sunday, December 16 at the Tennessee Williams Theater. Nutcracker is one of the largest, most elaborate stage productions ever to hit the Keys and a definite “Must See”
for the holidays.

Also not to be missed: the Holiday Historic Inn Tours where you can embark on a delightful tour of five decorated inns, enjoy traditional caroling and embrace the spirit of the season. On Saturday, December 15, the Key West Bight dazzles with a magical nautical display of lights during the 28th Annual Schooner Wharf Bar Lighted Boat Parade which sets sail at 8 pm in the historic Key West Seaport. The celebration wraps up on New Year’s Eve with wild celebrations all over the island including the lowering of a Pirate Wench from the soaring mast of the tall ship, Schooner America 2.0 at Schooner Wharf Bar.

But that’s just the half of it. For a complete schedule of holiday happenings, ticket info, and room bookings go to

Happy Holidays!