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A '12 Days of Christmas' Guide to Key West

Posted on: November 30th , 2023 | Events & Festivals
A '12 Days of Christmas' Guide to Key West

There’s nothing like sending holiday beach photos to relatives up north while they’re knee deep in snow. Aside from this Florida Christmas pastime, there are more Key West events and traditions that put locals and visitors in a holiday state of mind. Here are 12 days of Christmas events and activities you can’t miss out on this 2023 holiday season.

Although we strive to provide the most current information, attractions and events mentioned may be closed or canceled without notice. We recommend checking individual attractions for operating hours and updates before visiting.

Save up to 50% with our extended Black Friday/Cyber Monday sale

1. Holiday Village and BeLighted Christmas Bike Ride

Dec. 1, 4 - 8 p.m.

The 3rd annual Holiday Village & BeLighted Bike Ride kicks off the magical month of December at the Coffee Butler Amphitheater. The family-friendly Holiday Village includes photos with Santa, food, music, rides, local performances, an inflatable obstacle course, and community booths with games, crafts, and goodies for kids. You’ll need to purchase tickets to the Holiday Village, but anyone can glimpse the decorated bikes as the BeLighted Bike Ride treks from Whitehead to Duval Street.

2. Hometown Holiday Parade

Dec. 2, 7 p.m.

For a small-town local feel, the Hometown Holiday Parade features local high school bands and festive floats. The parade starts at Truman Avenue (at White Street) and continues down Duval Street to Eaton Street.

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3. Pilates & Prosec-HOHOHO, followed by Schooner Wharf Bar Tree Trimming Party

Dec. 3, 10 a.m. (Pilates & Prosec-HOHOHO), 6 p.m. (Tree Trimming Party)

Grab your Christmas sweaters and join 24 North Hotel for a FREE 30-minute Hot Pilates class on the Sunset Green Event Lawn. Strengthen and stretch your body during the special holiday session, and stick around for a live DJ and pop-up-shops after your workout.

Later, hotel guests can jump on 24 North Hotel’s shuttle to Old Town. Christmas comes early at Schooner Wharf, as locals and visitors gather to trim the bar’s holiday tree during their annual Tree Trimming Party (those who help trim get a free cocktail!). Help decorate the tree with ornaments (make and bring your own to be entered into a contest), donate an unwrapped present for the Toy Drive, and enjoy live holiday music and seasonal drinks like Swedish glögg, Hot Applejack, and Eggnog with rum.

4. Old Town Trolley’s Holiday Sights & Festive Nights Christmas Tour

Dec. 8 - 23, 6:30 p.m., 7 p.m., 8 p.m., and 8:30 p.m.

Want to see the historic Key West homes in all their lighted glory? This is fun for the whole family. The Old Town Trolley offers evening tours from Mallory Square on select nights and times throughout December. Buy tickets in advance.

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5. Harbor Walk of Lights

Now through New Year’s Eve

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 held every evening from dusk to dawn throughout the holiday season.

6. Holiday Concert & Bazaar at Custom House Museum

Dec. 8, 5 - 9 p.m.

The free annual Holiday Concert & Bazaar returns to the sweeping historic porch of the Custom House Museum with local artisans, musicians and choirs, food and libations, Santa selfies, and a magical holiday light show designed by Key West High School’s Conch 5 Studios.

7. Schooner Wharf’s 32nd Annual Key West Lighted Boat Christmas Parade

Dec. 9, 8 p.m.

In Key West, we “deck the hulls” for this annual Christmas Boat Parade. 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 prizes and free raffles up for grabs. The procession begins at 8 p.m. on Dec. 9, 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.

8. Eaton Street Christmas Stroll

Dec. 10, 3:30 - 7:30 p.m.

From Whitehead to Simonton, Eaton Street in Key West will transform into the North Pole for one night only in December. Participating venues like Williams Hall, Tropic Cinema, Key West Theater, and the Key West Library will have open doors, as guests are invited to stop in for holiday entertainment like concerts, classic cartoons, festive cocktails, and winter exhibitions. Admission is free, but tickets are required through Tropic Cinema.

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9. Waterfront Winter Wonderland

Dec. 15 - 30

Ice skating in Key West? The Waterfront Winter Wonderland coming to the Coffee Butler Amphitheater at Truman Waterfront Park will have one. The two week-long holiday celebration is fun for all ages, and will also feature games, thrilling rides, attractions, music, light displays, photo opportunities and letters to Santa, a vendor village, and more. Admission is only $10 and kids under five are free.

10. 15th Annual Rudolph Red Nose 5K Run

Dec. 16, 8 a.m.

Don your favorite Christmas pajamas and join fellow runners at the Southernmost Beach Café for the annual Rudolph Red Nose 5K. Afterwards, enjoy refreshments, prizes for best festive or most unusual 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.

11. Christmas Shopping at the Key West Artisan Market, followed by the “Holiday Classic Car Show” at Conch Republic Seafood Co.

Dec. 17, 10 a.m. - 2 p.m. (Market), 11 a.m. - 3 p.m. (Car Show)

Check off everyone on your shopping list at the island’s local festive markets and artisan boutiques. The Key West Artisan Market at Truman Waterfront Park is dedicated to spotlighting the best local makers, mom-and-pop businesses, and vendors in the Keys and South Florida. Check out more of Key West’s one-of-a-kind boutiques to snag the perfect Christmas gifts with our Very Key West Holiday Gift Guide.

From Truman Waterfront Park, you’ll have to book it to Conch Republic Seafood Company on the Harbor Walk of Lights at Greene and Elizabeth Street to see the Holiday Classic Car Show, where classic cars from every era will be lined up and 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, “Best in Show”, and more.

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12. Christmas Day Cruise aboard Fury Catamaran

Dec. 25, 9 a.m.

Open your presents early, because Fury Water Adventures departs in the morning for a Christmas cruise aboard their spacious, state-of-the-art catamaran. The all-day Christmas excursion includes a Banana Boat ride, a snorkeling experience around North America’s only living coral reef, Key West’s largest ocean water park, a special holiday-themed menu with complimentary drinks, and so much more.

Enjoy your island holiday getaway with a longer stay at 24 North Hotel. See which of our specials works for you. If you’re traveling to Key West without a car, we offer continuous shuttle service into town and so much more. Happy Holidays!

Now for a limited time, save up to 50% with our extended Black Friday / Cyber Monday sale. Offer expires Dec. 1 

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Joining us in December? See what our past guests had to say about their holiday visit:

“At the last minute, we reserved a room at 24 North. Best thing we ever did. The hotel is beautiful, has a bar in the lobby with the most congenial bartender ever. There is breakfast and a lovely pool area. Extremely affordable, especially at Christmas. Love it, would go back in a heartbeat.” 5/5 - Patandeddie, TripAdvisor

“[24 North Hotel]…was great, my family and I had a great time staying there for the holidays.” 5/5 - Romano Dormainvil, Google Review

“[24 North Hotel]...is the best. They have the most fun events and really care about their community. We are locals and always come to the fun events on the lawn. They had Santa and a snow machine and face paint at the light up Christmas tree event and free tropical vibes snow cones!” 5/5 - Erin S, TripAdvisor

“Christmas in the Keys. Had a great stay…staff at the front desk are very helpful. Would definitely go back and stay for a third time!!!! Enjoyed hanging by the pool and the drinks at bar. Coconut Creamsicle, Yum!” 5/5 - Vacatime777, TripAdvisor

“Key West Christmas! This was my first time to Key West. Staying at 24 North was relaxing and my every need was met. The Flying Pig Food Truck was on the property and the food was wonderful. The pool was very clean. I highly recommend!” 5/5 - TL Emmert, TripAdvisor





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