There’s nothing like sending beach photos to relatives during the holidays while they’re up north knee deep in snow. 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 2021 holiday season.
Although we strive to provide the most current information, attractions and events mentioned may be closed or cancelled without notice. We recommend checking individual attractions for operating hours, updates, and safety measures before visiting.
Harbor Walk of Lights
The Harbor Walk of Lights stretches along the seawall past Greene, William, and Margaret Streets to the K.W. Ferry Terminal - which are completely lit-up in pure island fashion! Take a photo with nautical-themed Christmas trees which honor the maritime history of the Key West waterfront. Visitors can enjoy local shops, eats, and drinks on the harbor while taking in the holiday spirit. The event is every evening from dusk to dawn throughout the holiday season.
Key West Holiday Lights & Sights Tours
Want to see 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 from Mallory Square on select nights throughout December. Buy tickets in advance.
Christmas Shopping in Key West
Check off everyone on your gift list at local festive markets and artisan boutiques. The Key West Artisan Market is dedicated to spotlighting the best local makers, mom-and-pop businesses, and vendors in the Keys and South Florida. The Studios of Key West is also supporting community artists and small businesses by hosting a Holiday Artisan Market completely online. Visit their online shop through Christmas Eve to shop works from 25 unique local artisans specializing in jewelry, textiles, home accessories, and more. Check out more of Key West’s one-of-a-kind boutiques to snag the perfect Christmas gift with our Very Key West Holiday Gift Guide.
Santa at the Shops at Mallory Square
See Santa at the Shops at Mallory Square on select dates throughout December (Dec. 4, 11, 18, and 19 from 11 - 3 p.m.). Santa will be in the North Pole located upstairs in the historic shops to hear all of your Christmas wishes!
Hometown Holiday Parade
For a small-town local feel, the Hometown Holiday Parade features local high school bands and floats on Dec. 4 at 7 p.m. The parade starts at Bayview Park and continues down Duval Street to Eaton Street.
The Conch Republic Seafood 2021 “Holiday Classic Car Show”
Visit the Conch Republic Seafood Company at Greene and Elizabeth Street to see classic cars from every era decked out for the holidays. Guests can see who takes home the top awards and get the opportunity to vote for “People's Choice” for best engine, interior, original and custom, and “Best in Show”. The free event will be held on December 5 from 11 a.m. - 3 p.m. For more information, visit the Holiday Classic Car Show.
Schooner Wharf’s 30th 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. 11, with viewing along the Harbor Walk of Lights and the Historic Seaport. Arrive at the Key West Bight early to take in holiday music, shopping, and dinner. More info here.
Sugar Rum Cherry: A Burlesque Nutcracker
Inspired by the Tchaikovsky holiday classic “The Nutcracker”, this burlesque parody is the adult version we’ve all been waiting for! See the performance December 15 - 17 at the Key West Theater. Click here for tickets.
13th Annual Rudolph Red Nose 5K Run
Don your favorite Christmas pajamas and join others December 18 at 7 a.m. at the Southernmost Beach Café for the annual run. Afterwards, enjoy refreshments, prizes for best festive pajamas, and a silent auction. Proceeds benefit A Positive Step of Monroe County, a non-profit organization serving high risk kids and families since 1999.
Set Sail on Christmas Day
There are a few Christmas Day sails happening in Key West. Schooner America 2.0 is a two-hour Christmas Day brunch that features complimentary boozy drinks along with offerings like spiral-cut ham, bagels and pastries, meats and cheeses, smoked salmon, crudités, and other delicious Christmas day treats aboard the 1851 revival sailboat. Fury Water Adventures is hosting a ‘Christmas Ultimate Adventure’ of its own. Climb aboard their spacious catamaran for an all-day Christmas excursion which includes a Banana Boat ride, snorkeling, a special holiday-themed menu, and so much more.