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Key West Holiday Events Calendar

by Keith langston
Key West Santa

Key West is loaded with excellent holiday events for both Christmastime and New Year's Eve

Image: Rob O'Neal/Florida Keys News Bureau

Key West is one of the most unique and fascinating destinations in all of America. On top of that, it’s an island that loves to have a good time and is always down for another celebration. So, naturally, its residents get excited for the holidays. Throughout December, leading up to Christmas and the New Year, there is tons do, see, and experience in America’s little slice of paradise. Here are some must-attend events during this holiday season in Key West.


The Harbor Walk of Lights

Nightly until New Years

Key West Harbor Lights (Photo: (Rob O’Neal/Florida Keys News Bureau))

For the most Key West Christmas ever, you need to visit the Harbor Walk of Lights. The displays are lit every night until New Years along the Harbor Walk. Artists come and decorate nautical treasures like buoys and lobster traps and adorn them with twinkling lights, ornaments, garlands, and more. Even the surrounding palm trees get decked out with thousands of Christmas lights. It’s the perfect place to take a beautiful (and cheeky) stroll along the waterfront after a nice dinner.


Lighted Boat Parade

December 11

Lighted boat parade

The Lighted Boat Parade (Image courtesy of the Florida Keys and Key West)

Taking place at Schooner Wharf is the 30th annual Lighted Boat Parade, which is being put on this year by Schooner Wharf Bar and Absolut Vodka. The parade includes dozens of boats, from dinghies to fishing vessels, and even tall ships, all decked out in stunning light displays. A panel of judges will be rating the boats and a winner gets chosen by the night’s end. All the bars, restaurants, and resorts on the wharf will be open and make for excellent viewing spots for the festivities. The evening will also include a steel band performance starting at 6 pm.


Holiday Lights Tours

December 12 – 26

Avalon Bed and Breakfast

The Avalon Bed and Breakfast featured on the tour (Image courtesy of the Florida Keys and Key West)

The Conch Tour Train, a famous trolly in Key West, offers unforgettable hour-long Holiday Lights Tours of the island during the holidays. The tours go through elaborately decorated neighborhoods, pass by gorgeously festive hotels and inns, and even include caroling! It’s an excellent way to see the town illuminated with festive cheer. Plus, special holiday glasses are included for all passengers. The Conch Tour Train can even arrange for private holiday lights tours for large groups and families.


Sugar Rum Cherry: A Burlesque Nutcracker

December 15 – 17

Sugar Rum Cherry

Sugar Rum Cherry performance (Photo courtesy of Key West Burlesque)

For those wanting some adult entertainment, the Key West Theater will be performing Sugar Rum Cherry: A Burlesque Nutcracker from December 15-17. According to the production’s website, it will be filled with a “bevy burlesque beauties who dance their way through the land of libations in an adult version of the holiday classic, The Nutcracker.” It’s sure to be a rollicking and unique twist on the classic Christmas ballet that you won’t be able to see anywhere else. Tickets are on sale now and start at $50.


Rudolph Red Nose Run

December 18

Christmas 5k run

Rudolph Red Nose Run (Photo: John Dvorak)

On Saturday, December 18th, walkers and runners of all ages are encouraged to take part in the 13th annual Rudolph Red Nose Run. The 5k run helps raise money for the APSMC, a Florida Keys nonprofit that provides services for at-risk youth and their families. It’s not uncommon to see runners wearing red noses or even dressing up for the occasion (this year’s theme is “Holiday Jammies”). It’s a fun and festive way to help give back to the community (and have one hell of a cardio workout!) After the race, there will be prizes, snacks, and a silent auction.


New Years Events

December 31

Key West high heel drop

Key West drag sensation, Sushi, rides the famed high heel on New Years (Photo: Andy Newman/Florida Keys News Bureau)

New York City might have the famous ball drop to herald in the new year, but Key West has not one, but three “drops” of its own.

Conch Shell Drop – the world-famous Sloppy Joe’s bar holds an annual conch shell drop. The entire day is abuzz at Sloppy Joe’s, with live music beginning at noon. Throughout the day and night, local beers and cocktails will be served to a jovial crowd, all leading up to the famous conch shell drop, which takes place on the bar’s roof. The streets surrounding the bar become amassed with spectators all looking to welcome the new year with good friends and great music.

Pirate Wench Drop – For those who prefer the company of a more swashbuckling crowd, the Schooner Whar Bar will be holding their annual New Years festivities on the 31st as well. Starting earlier in the evening, a DJ will be spinning tunes and the bar will be serving drinks, all in anticipation of 2022. Per tradition, all patrons will sing Auld Lang Syne in the minutes leading to midnight, at which point Evalena Worthington, the bar’s resident tavern wench, will drop down alongside illuminated numbers on the mast of a tall ship, welcoming in the new year. But the party doesn’t end there. The bar will be open until 4 a.m. and complimentary hats, horns, and party favors will be distributed before the big event.

High Heel Drop – Key West’s famous LGBTQ bar, the Bourbon Street Pub, has been dropping drag queens in a giant high heel shoe since 1996. It’s easily Key West’s most fabulous way to usher in the new year. Dance to music, drink great cocktails, and party next to go-go boys, drag queens, and Key West’s eclectic LGBTQ community in a stunning and unforgettable night at one of the city’s most famous establishments.

For a full list of holiday events taking place, check out Key West’s official calendar of events.

Be Sure to Explore More:

Destination: Key West

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