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Best 9 things to do in Key West in December 2019


It’s the most wonderful time of the year, and this December’s events reflect exactly that.

From celebrating New Year’s Eve on a sub-tropical island, to eating fresh seafood and watching a parade full of Dashchunds, this Decemeber in Key West will be quirky and cultural, as it should be.


 1. Explore The “Brooklyn Of Key West”

I LOVE Stock Island Festival Graphic 2017

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Stock Island, our closest neighbor, is sometimes lovingly referred to as an old Key West, what the town felt like in the 70s. December (TBA), Stock Island will come alive with a 3 day event, Dec 7th-9th, both free and ticketed, showcasing the community’s culinary, entertainment, artistic, cultural & historic gems. See the list of events here


2. Run A Triathlon

The Key West Triathlon, now in it’s 9th year, attracts athletes from all over to compete in paradise. With 1,000 contestants, it’s a “big race on a little island.” The best part? The swimming portion in the ocean is much warmer compared to other races around the world this month. The races happen December (TBA).


3. Join The Lighted Bike Parade

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A fun event benefiting holiday toys for needy kids, hundreds of people will ride bikes with lights through the streets of Key West. Registration for the ride is one unwrapped toy for the Key West Holiday Store. The show hits Key West on December (TBA) at Bayview Park.


4. Tour Historic Inns

Ten historic inns will be festively decorated for the holidays on this self-guided tour on both December 28th & 15th. Treats with jolly will be sampled at the properties and a trolley will be provided for guests.


5. See the Nutcracker Key West-style

Photo // Youtube

Inspired by the unique and colorful environment of the Florida Keys, Clara and her young Prince encounter enchanted landscapes complete with snowy egrets on shimmering salt ponds, a wicked Rooster-King, an exquisite Sea-Star Fairy, and “underwater” sequences of almost unimaginable beauty. Local children, adults and community leaders are cast alongside a nationally-cast corps de ballet in this spectacularly crafted semi-annual production of a beloved classic. Shows held at the Tennessee Williams Theatre.


6. Watch The Lighted Boat Parade

The family-friendly annual boat parade is a locals favorite. Watch as tall ships, yachts, row-boats and everything in between float along the historic seaport.


7. Get in the Christmas “Spirit” on a Cocktail Crawl

Our tour encompasses a lot more than just drinks. Discover the local haunts and how the Hemingway Daiquiri was invented, as we walk through historic neighborhoods from restaurant to restaurant.


8. Delight In A Dachshund Parade

Photo // Rob O’Neal/Florida Keys News Bureau

Yes, you read that right. Key West is always looking for an excuse to have a parade on Duval street, so naturally, on December 31st, a dachshund walk was assembled more than a decade ago. Look out for the Chihuahua flash mob while you’re there.


9. Celebrate A Tropical New Year’s Eve

Photo // The Key West Citizen, Rob O’Neal MIAMI HERALD OUT

2018 isn’t officially over until a drag queen drops down in a red stiletto. Other drops around town include a wench, conch shell, cuban cigar, and key lime wedge. But the icing on the cake is drinking champagne in 75 degree weather.