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Best 9 things to do in Key West in December 2020



Please keep in mind that many of these events are reoccurring and will likely be back in business 2021!  Our tours are still running, though! Click here for our tour calendar!

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”

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 13th-15th, 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 7th.


3. Join The Lighted Bike Parade

Photo //

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 4th 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 27th & 28th. Treats with jolly will be sampled at the properties and a trolley will be provided for guests.


5. See the Nutcracker Key West-style

A naughty and spirited two-actreverie, inspired by the famed Tchaikovsky holiday classical “The Nutcracker” ballet, is sure to bring laughter to Key West’s holiday festivities. Clara, a young ingénue, celebrates the season with one to many sugar rum cherry cocktails. That night she dreams of sword fights and sailors and a world unlike any other in the “Land of Libations”. The show stars Tatah DuJour, Moana Amour, Jenna Beth and Auroura Natrix. December 19th. Click here for tickets 


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. December 14th @ 8pm.


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. Holiday Evening of Dance


What was once supposed to take place in April is now set for the day after Christmas! The Key West Blues Festival returns with Key West’s blues performers to offer you an exclusive concert experience in its second year. You can look forward to seeing some of Key West’s best blues musicians such as Bill Blue, Caffeine Carl, Ericson Holt, and more. Grab your tickets now! 


9. 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.


CANCELED: BONUS! Celebrate A Tropical New Year’s Eve

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

Can 2020 end any sooner? This weird year 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….however don’t get too excited yet, many of these festivities ares sure to be cancelled until 2021…but we can drink to that!