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Christmas in Key West

Posted on: November 1st , 2019 | Events & Festivals
Christmas in Key West

There’s nothing like sending beach photos to relatives during the holidays while they’re up north freezing their wits off. Aside from this Christmas pastime, there are more Key West traditions that put locals and visitors in a holiday state of mind. Here are some activities you can’t miss out on this 2019 holiday season.

Schooner Wharf’s 29th Annual Key West Lighted Boat Parade

Other cities and towns have ice skating around Christmas time, but in Key West we “deck the hulls” for this annual holiday boat parade. The procession begins at 8 p.m. on Dec. 14, with viewing along the Harbor Walk of Lights and the Historic Seaport. Boats of all sizes are decorated with lights, precision and care to impress spectators, but, most importantly, the judges at Schooner Wharf Bar & Galley, as there’s over $20,000 in prizes and free raffles up for grabs. Arrive to the Key West Bight early to take in holiday music, shopping and dinner. More info here.

Harbor Walk of Lights

The Harbor Walk of Lights will  Nov. 27, with the Harbor Walk at Greene and Elizabeth Streets completely lit-up in pure island fashion. Take a photo with nautical-themed Christmas trees –. You can’t see this kind of stuff anywhere else! The Harbor Walk of Lights will be lit through New Year’s Eve. Visitors can enjoy local shops, eats and drinks on the harbor while taking in the holiday spirit.

Key West Holiday Lights & Sights Tours

Want to see all the cute Key West homes in all their lighted glory? This is fun for the whole family. The Old Town Trolley offers hour-long evening tours beginning at 6 pm. from Mallory Square in December. Cookies and cider will compliment your open-air trolley tour of Christmas lights in Old Town. Buy tickets in advance.

Hometown Holiday Parade

For a small-town local feel, the hometown holiday parade features local high school bands and floats on Dec. 7 at 7 pm. The parade starts at Bayview Park and continues down Duval Street to Eaton Street.


If you’re traveling to Key West without a car, make sure to check out specials at 24 North - we offer continuous shuttle service into town and much more.

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