Spending the end of 2023 with us here in Key West? Here are some of the best annual holiday activities and Christmas events to look forward to year after year.

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.

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Harbor Walk of Lights

Nov. 22 - New Year’s Eve

Get your annual dose of Christmas lights along the seawall of the Key West Bight during Harbor Walk of Lights, on display every evening through New Year’s Eve. See the Christmas tree made of buoys, another made of lobster traps, and more maritime holiday decorations during this annual set-up. Visitors can enjoy local vendors, eats, and drinks on the harbor while taking in the holiday spirit. This year’s display includes a special tribute to Jimmy Buffett.

Lighting of the Tree Celebration: Holiday Celebration on Sunset Green Event Lawn

Nov. 29, 5 - 8 p.m.

Join The Gates Hotel for a magical evening at our Lighting of the Tree Celebration on Sunset Green Event Lawn. Admission is FREE, so bring your friends and family for a festive night out. Capture the holiday spirit in photos with Santa and indulge in delicious food and drink specials. Plus, we'll have local vendors on site and a build-your-own hot chocolate bar benefitting MARC House. Come together as a community and kick off the holiday season with us! 

Holiday Village and BeLighted Christmas Bike Ride

Dec. 1, 4 - 8 p.m.

Head to the family-friendly Holiday Village at the Coffee Butler Amphitheater in Truman Waterfront Park at 4 p.m. on Dec. 1 for over 20 community booths offering games, goodies, crafts for kids, bounce houses, a DJ, food trucks, and pictures with Santa. Afterwards, decorate your bike with lights and participate in the BeLighted Bike Ride which will roll through Old Town at 8 p.m. Get your tickets in advance.

Pet Pictures with Santa

Dec. 1, 6 - 8 p.m.

Bring your furry friend to the 16’ Nautical Christmas Tree on the Harbor Walk of Lights at William Street to get some professional shots with Santa. Pictures are $25 (cash only) and benefit the local Boys & Girls Club. Stick around until Dec. 9 at 10 a.m. for the 10th Annual Parade of Paws & Holiday Bazaar at Higgs Beach.

At The Gates Key West, we understand that your doggo is an important companion, family member, and best friend. That is why we are a dog-friendly hotel! Check out the best dog-friendly restaurants in Key West.

Hometown Holiday Parade

Dec. 2, 7 p.m.

For a small-town feel, the Hometown Holiday Parade features local high school marching bands, charming floats, and an appearance by Santa. The Christmas parade starts at Bayview Park at Truman Avenue and White Street and continues down Duval Street to Eaton Street.

Monthly Artisan Market

Dec. 3 and 17, 10 - 2 p.m.

Back for the season, the Key West Artisan Market is a good place to pick up local, handcrafted holiday gifts for your loved ones. The market’s seasonal edition will feature textiles, jewelry, foodstuffs, and more. This is a nice way to start a Sunday morning and pick up local goods you won’t find anywhere else. Open from 10 - 2 p.m. at Higgs Beach on Dec. 3 and 17.

Pilates & Prosec-HOHOHO

Dec. 3, 10 a.m.

Grab your Christmas sweaters and join The Gates 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.

Old Town Trolley’s Holiday Sights & Festive Nights Tour

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

Take in the cascade of lights and holiday decor of Key West’s historic homes on Old Town Trolley’s annual Holiday Sights & Festive Nights Tour. Each year, the historic homeowners participate in the friendly competition of going all-out on holiday decorations to see which one of them will win bragging rights and the $500 top prize. The 60-minute trolley tour also includes a fun narration with facts about the island.

Holiday Concert & Bazaar at Custom House Museum

Dec. 8, 5 - 9 p.m.

This 7th annual festive party features Key West’s finest artisans with a trove of unique gift options, musicians and choirs, food and libations, Santa selfies, and the popular holiday light show designed by Key West High School’s Conch 5 Studios, which will be projected on the face of the Custom House. The free Holiday Concert & Bazaar will be held on the sweeping historic porch in front of the Key West Museum of Art & History.

Key West Schooner Wharf Lighted Christmas Boat Parade

Dec. 9, 8 p.m.

Don’t miss this tropical tribute to the holiday season. Boats of all sizes are decked out with lights - and with boatloads in prizes for best decorated, no detail is overlooked. Held at the Schooner Wharf & Bar, the 32nd annual Lighted Boat Parade begins at 8 p.m. on Dec. 9, with viewing along the Harbor Walk of Lights and the Historic Seaport.

Eaton Street Christmas Stroll

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

Eaton Street becomes the southernmost North Pole for the annual Christmas Stroll, giving passerby the opportunity to wander the blocks between Whitehead and Simonton with stops at Williams Hall for a concert from the Bahama Village Music Program, Tropic Cinema for some classic cartoons, The Studios for cocktails, St. Paul’s for a traditional Christmas concert, The Studios of Key West for a winter exhibition, and so much more. Admission is free, but tickets are required via Tropic Cinema.

Menorah Lighting Ceremony at Bayview Park

Dec. 10, 5 p.m.

The City of Key West’s Menorah Lighting Ceremony will be conducted right before sunset, signaling the beginning of Hanukkah. Find Bayview Park in the center of Key West, on the corner of Truman Avenue and Georgia Street.

Waterfront Winter Wonderland

Dec. 15 - 30

The Coffee Butler Amphitheater at the Truman Waterfront Park will transition into an illuminated Winter Wonderland for all ages with an ice skating rink, games, rides, attractions, music, light displays, a vendor village, and more. The two weeks of fun at the Waterfront Winter Wonderland will include themed skate nights, live music performances, and photo opportunities and letters to Santa. Admission is $10, kids under five are free.

15th Annual 5K Rudolph Red Nose Run

Dec. 16, 8 a.m.

Wear your festive holiday pajamas and join A Positive Step of Monroe County’s 5K Rudolph Red Nose Run. The race begins and ends at the Southernmost Beach Café on Duval Street, followed by post-race refreshments, prizes, and a silent auction.

Holiday Classic Car Show

Dec. 17, 11 a.m. - 3 p.m.

The Florida Keys Southernmost Car Club will host the Holiday Classic Car Show outside the Conch Republic Seafood Company with cars from every era decorated for the holidays. Vote for best sports car, pick-up, engine, interior, original and custom, pre and post 1950, and best in show.

Peter Mayer: Stars & Promises Christmas Tour 2023

Dec. 20, 8 p.m.

You may know Peter Mayer as the lead guitarist in Jimmy Buffett’s Coral Reefer Band, having worked alongside the beloved late musician since 1988. Of course, his talents go far beyond his work with Buffett, releasing 25 albums to date and touring year round with the Peter Mayer Group. See the talented musician at the Key West Theater for his Stars & Promises Christmas Tour.

Fireworks Celebration and The Marshall Morlock Band

Dec. 30, 6 p.m.

We’re kicking the New Year off early with an epic party and fireworks celebration on the Sunset Green Event Lawn. Come 6 p.m., there’s food, drinks, and a performance by The Marshall Morlock Band, followed by a dazzling fireworks show that will light up all of New Town. A portion of your food and beverage purchases will go straight to the Highgate Charitable Foundation.

New Year’s Eve

Dec. 31

Key West goes all out on New Year’s Eve, and this year will be no exception. Countdown to 2023 at the Shoe Drop with Sushi at Bourbon Street Pub, Lowering of the Pirate Wench at Schooner Wharf, or the Conch Shell Drop at Sloppy Joe’s, with a special fireworks show at White Street Pier on the Key West Harbor side of the island.

Spending the holidays in Key West? See hotel rates at The Gates Hotel Key West, a Conde Nast award-winning Key West destination which offers shuttle service to Old Town, a beautiful pool, and on-site food and drink services.

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