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Things to Do in Key West in December

Things to Do in December Blog

There’s nothing quite like the holidays in Key West. Where else can you enjoy warm winter weather, water sports and palm trees wrapped in twinkling holiday lights? Whether you’re here during one of the big December holidays or simply taking an end of the year vacation, there are plenty of things to do in Key West in December.

Key West Holiday Parade

December 3

October’s Fantasy Fest parade might get all the attention, but Key West also hosts a festive, family friendly holiday parade every December. With floats and marching groups representing local churches, civic organizations, businesses and schools, it’s a fantastic way to celebrate the holiday season. Find a spot to watch on the main drag of Duval Street or anywhere along the parade’s route on Truman Street.

Key West Triathlon

December 3

The annual Key West Triathlon brings 1,000 athletes to the southernmost point for this inspiring competition that includes running, cycling and swimming. Key West’s mild winter temperatures make for the perfect conditions both on land and in the water. Those who register can choose between Olympic and Sprint distances.
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Holiday Tours on the Trolley 

Select Nights December 9-24

Key West might not turn into a snowy winter wonderland in December, but that doesn’t mean the residents don’t go all out with the holiday decor. Hop aboard Old Town Trolley or Conch Tour Train for their annual holiday lights tours. Ride around town oohing and aahing at twinkling lights, garlands, props and other decorations. And these 60 minutes tours aren’t just about the sights, be sure to grab a few cookies and a glass of cider for the road! This annual holiday tradition is a hit with every member of the family and is sure to put you in the holiday spirit.
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Schooner Wharf Bar Annual Lighted Boat Parade

December 10

The Lighted Boat Parade is Key West’s signature holiday event. Picture beautiful schooners, fishing yachts, catamarans and even kayaks bedecked in holiday lights floating tranquilly through the Key West Harbor. It’s how Key West gets into the holiday spirit in true island life style. Find a spot along Mallory Square or the Historic Seaport to take it all in. At Fury Water Adventures, you can also hop aboard our spacious 65-foot catamaran and be a part of the parade!
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Sail With Santa

Fury’s Annual Sunset Sail with Santa Benefiting Wesley House

December 16

For subtropical holiday cheer, join us aboard our annual Sunset Sail with Santa benefiting Key West’s Wesley House. Children 12 and under sail for free and we ask for a minimum $20 donation from adult participants. Trek the Key West waters with us and enjoy complimentary beer, wine, champagne and holiday snacks. And, of course, Santa will be there! It’s fun for the whole family and benefits a great cause.

Monthly Artisan Market

December 18

For those looking to do some shopping, head on over to the Restaurant Store on Eaton Street for the monthly Artisan Market. This month’s theme is Holiday Shop Local. Cruise the vibrant, open-air market filled with artists, chefs, authors, craftspeople and performers. Browse delectable treats such as fresh produce, baked goods, flowers, craft beer and wine.

Holiday Concert & Bazaar

December 21

This inaugural event held at the Custom House Museum is sure to put you in the holiday spirit! Join Key West’s finest artisans, musicians and choirs for a night of family-friendly fun. And what would a holiday festival be without a flashy light show? Do some last minute gift shopping while browsing hundreds of unique options while listening to live music, sampling delicious food and sipping on libations. This event is free to the public, including Santa’s helpers!

Fury Christmas Ultimate Adventure

Christmas Ultimate Adventure

December 25

In Key West for Christmas? Start a unique family tradition and enjoy Christmas at sea with Fury’s Ultimate Adventure trip. This full day trip includes breakfast and a special holiday lunch as well as unlimited beer and wine. You’ll go snorkeling, parasailng, jet skiing and more. Enjoy spending time with your loved ones while taking in Key West’s amazing December weather.
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Annual Key West House & Garden Tours

December 27 & 28

Part of Key West’s inherent charm rests in its lovely homes and Victorian-style architecture. During the Key West House & Gardens Tours, enjoy a self-guided exploration through some of Key West’s most beautiful homes while they’re all dressed up for the holidays. This casual and festive event is presented by the Old Island Restoration Foundation.
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Fury Last Sunset Sail

New Year’s Eve in Key West

December 31

Key West is always counted among the best places in the country to ring in the New Year—and for good reason. With warm, subtropical temperatures and a festive party atmosphere, it’s all laid back good fun here on New Year’s Eve. Start your evening with the last sunset sail of the year aboard one of our catamarans and then hit the town’s multiple bars and restaurants. And don’t forget about the various countdowns to midnight, all of which are done in true Key West style. You can watch the Conch Drop from Sloppy Joe’s, the Stiletto Drop from Bourbon Street Pub or the Wench Drop at Schooner Wharf.
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