Top 7 Things to Do in Key West in December 2019

Enjoy 7 Unique Holiday Activities on Key West

Escape the winter chill and hop down to Key West for a multitude of magical ways to celebrate the holiday season on the island. The inclusive and warm nature of Key West lends itself to be a perfect setting for getting into a holiday spirit.

Here are some of our favorite festivities this December:

Schooner Wharf Tree Trimming and Toys for Tots and Angels Just 4 Kids Drive

Kick off the holiday season with the locals at  Schooner Wharf Bar… craft your own nautical ornament to add to their tree (and maybe win a prize), enjoy live island music, peruse the craft fair, and bring an unwrapped toy for their toy drive! Trimmers and gifters receive a complimentary holiday libation! 


Sunday, December 1, 2019, 5 pm


Key West Lighted Bike Parade

Whether you want to hop on a bike and join the parade, or simply watch the sparkling fun go by, this is a wonderful way for the whole family to get the season rolling! A benefit Wesley House Family Services, this neighborhood parade features lighted and decorated bicycles. Registration is free with a toy drive donation. The fun begins at 7pm (check-in, 6pm) at Bayview Park, and ends at locals’ favorite hangout, Mary Ellen’s for a Block Party (free for riders)!


Wednesday, December 4, 2019, 6 pm 

Visit or registration, the new route, and other details. 

Key West Holiday Parade  

A Key West tradition, this family-friendly parade rivals the famous Fantasy Fest parade… full of floats, marching bands, and merriment marching through Old Town! Starting at White Street and Truman Ave, there are plenty of places to watch along Truman Ave and Duval, and plenty of candy raining down for one and all! 


Saturday, December 7, 2019, 7 pm

I Heart Stock Island Festival

Celebrate the ever-growing “Brooklyn” of Key West! Stock Island, our closest neighbor, has become the newest spot to experience “island living.” Explore three days of free and ticketed events featuring food, art, and entertainment, including Food Truck Finds, the 1st Annual Stock Island Lighted Boat Parade and Christmas at the Sheriff’s Animal Farm.




Nutcracker Key West  

If you think you’ve seen the Nutcracker one too many times, think again! This magical production at the Tennessee Williams Theater is a unique reflection of everything there is to love about Key West… tiny chickens, lively shrimp, and graceful snowy egrets. The magic of Key West is alive in this production, which is simply not to be missed.


Returning December 2020


Music at Martello presents Perpetual Groove w/ The Happy Dog Band

Thursday, December 12, 2019, 5-10pm Perpetual Groove creates a unique music experience for each live show. Experience the new chapter for Perpetual Groove that showcases the evolution of their music andlive performances. 


Thursday, December 12, 2019, 5-10pm 

New Year’s Eve in Key West

Monday, December 31 There is something for everyone when ringing in the New Year in Key West. You can march with the weiner dogs at the 14th Annual Key West Dachshund Walk during the day, and then you can countdown to midnight with the unique “ball drops” around the island. Who needs Times Square, when you can celebrate with a drag queen in a glittering high heel, a conch shell at the famous Sloppy Joe’s or a pirate wench down a ship mast at the seaport? There is no better way to welcome 2019 than here in Key West!


Monday, December 31

Thanks for checking out our Key West vacation tips. We look forward to celebrating the holidays with you!

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