December is a great time of year to visit Key West, the weather is typically the warmest place in the country.

1. Lighted Bike Parade

December 2: The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Key West for the holidays. At the Holiday Helpers Store, eligible parents walk through the store, empowered by the ability to pick free, new toys their children will want instead of just allocating non-specific toys to parents.

2. Key West Holiday Parade

December 3: Key West Annual Holiday Parade. Holiday spirit parades down beloved Duval Street the Holiday season begins. Civic leaders, churches, and other groups flow down Duval and through Old Town. It’s a Key West tradition. The parade starts at Truman and White at 7pm the first Saturday in December. Then it goes down Truman to Duval, to Caroline Street. There are around 50 entries each year, and the parade ends with Santa and Mrs. Claus bringing up the rear. There is a judges’ stand at the corner of Duval and Fleming streets.

3. New Year’s Eve in Key West

December 31: Key West is a great place for New Year’s Eve. We are typically the warmest place in the country, which means you can do more than the typical New Year’s Eve night out and dinner. Enjoy a boat day on the water like a local or one last sunset cruise. After dark, check out all the ball drops and parties for an unforgettable Key West New Year’s Eve.


4. Santacon Bar Crawl Key West

December 17: It’s the most wonderful time of the year! SANTACON 2019! Once again, our good friends at the Conch Republic Seafood Company are welcoming us for the event kickoff at 6pm. Then off to Tattoos and Scars at 7pm for the warm up to the great group photo on the steps of old City Hall at 7:50ish. Next stop, The World’s Smallest Bar to once again see how many Santas we can fit in there. Next is a new stop, Lucy’s Retired Surfers Bar on Duval. The at 9pm, It’s off to Cowboy Bill’s for Santa bull riding and pole dancing. and finally, when ever you stumble that way, end the evening as all good evenings do, at the Green Parrot.

5. Have a vacation of a lifetime! Spend the Day like a Local, on the Water

Everyday 🙂 Spend your vacation on the water, like a Key West Local! Enjoy the local sandbars and remote islands, with a remote beach sandbar charter or rental boat. Have a vacation of a lifetime! Or, try one of our many watersports.

6. Key West Lighted Boat Parade

December 10: Key West always does things a little different (better). When it comes to the holidays, the Lighted Boat Parade is no exception. This Key West parade event features boats of all kinds – big, small, with motors or sails, even kayaks. All decorated to the hilt with fantastic light creations. Book your spot and be in the parade.

7. Custom House Holiday Concert & Bazaar

December 9: Get into the holiday spirit with Key West Art & Historical Society’s Holiday Concert & Bazaar on Thursday, December 19th from 5PM to 9PM, located on the sweeping historic porch and promenade of the Custom House Museum. The celebration will feature Key West’s finest artisans, musicians and choirs, along with a spectacular holiday light show, with proceeds to benefit the Society’s programs. Learn more…

8. 63rd Annual Key West Home Tours

December 27 and 28: The annual Key West Home Tours™ are one of the oldest and longest running home tours in America, with the first tour in 1960. Old Island Restoration Foundation (OIRF) conducts the tours and they are funded in part by our generous supporters. Each tour features lovely homes and gardens reflecting the varied tastes and originality of their owners. Learn more…

9. Annual Key West Dachshund Walk

December 31: Annual Key West Dachshund Walk. Pups bring their people from near and far to parade down world famous Duval Street. It’s a short parade…costumes are encouraged, and please remember to bring a bag of dog food for the local Pet Pantry. No registration required.

10. Old Town Trolley’s Holiday Lights Tour

Select nights from December 6-23: Want to know the best way to see all the holiday lights across the island? It’s the Holiday Lights & Sights Tour presented by Old Town Trolley. Enjoy cookies, cider and a 60-minute Key West tour that is sure to put you in the holiday spirit. Check out the Sunset Celebration in Mallory Square, and then jump on the trolley at 6:00pm for the start of your tour.


11. Try Something New!

Looking to try a new Key West bar or restaurant since your last visit? We’ve got your covered. New Key West bars and restaurants.



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