Top Things to Do in Key West, Florida This December 2016

Florida’s Key West shows us that you don’t have to have snow and cold weather to have tons of winter fun. The people of Key West celebrate the holiday season in their own unique way, as only a tropical climate would allow it. If you’re heading this part of Florida to escape the winter cold, check out these top things to do in Key West this coming December.

Key West Holiday Parade

Where: Bayview Park
When: December 3, 2016

This holiday season doesn’t really begin in Key West without the annual Key West Holiday Parade. Every year, the parade ushers in the season with a procession of brightly lit floats, muscle cars, marching bands, and people in festive holiday costumes. Just as with previous years, the parade will run the length of Truman Avenue starting at Bayview Park. The Key West Holiday Parade will be on December 3, 2016, from 7:00 PM to 9:00 PM.

26th Annual Schooner Wharf and Galley Lighted Boat Parade

Where: Key West Bight
When: December 10, 2016

Because of Key West’s long and deep seafaring roots, it comes as no surprise that they honor that legacy of the sea in their holiday festivities. Thus, they have the annual Schooner Wharf and Galley Lighted Boat Parade, where motorboats and sailboats parade the length of Key West Bight bedecked in brilliant lights and colorful Christmas décor, accompanied by live music. Participants to the parade vie for cash and gift prizes and, more importantly, bragging rights. The annual boat parade is a long-standing tradition in Key West, returning on December 10 at 8:00 PM. Don’t miss this event that’s been top of the things to do in Key West in December for 26 years.

3rd Annual Parade of Paws and Holiday Bazaar

things to do in key west: parade of paws

Where: Higgins Beach Dog Park
When: December 10, 2016

If you’ve got a furry friend with you while you’re vacationing in Key West, why not join the Parade of Paws at Higgs Beach Dog Park? There, you can meet other passionate dog and cat friends and get a chance to have your pet be crowned as king, queen, prince, princess, duke or duchess of the parade. It’s also your chance to support the Florida Keys SPCA’s Animal Care Fund, which helps take care of homeless animals in Key West. If you don’t feel up to joining the parade, you can browse the pop-up stalls at the Holiday Bazaar for yummy snacks and maybe one-of-a-kind Christmas gifts for your family.

The Nutcracker Key West

things to do in key west: nutcracker key west

Where: Tennessee Williams Theater
When: December 10-18, 2016

The biannual performance of The Nutcracker is one of the more recent traditions the people of Key West have for celebrating the yuletide season. This 2016, from December 10 to 18, this community production of The Nutcracker Key West returns to the Tennessee Williams Theater to regale the audiences with the tale of Clara’s journey to the land of the Sugar Plum Fairy, a tale spun with rich, Key West tropical imagery. The cast for this year will be made up of 60 child and adult performers from the Key West community as well as 15 professional dancers from international dance companies.

56th Annual Key West House & Garden Tour

things to do in key west: hemingway house
Hemingway cat and house. From the Dale McDonald Collection. | Flickr Commons

Where: Oldest House & Garden Museum
When: December 27-28, 2016

One of the many charms of Key West is its Old Town district, full of grand old mansions mostly built in the Victorian style adapted to the conditions of living in Key West. These old houses, many of which are still privately owned, offer a glimpse into the community’s past with their collection of antiques and treasures. The Old Island Restoration Foundation gives you a chance to view some of these old houses at its annual Key West House & Garden Tour, happening on the 27th and 28th this December. Among the stops included in this walking tour are the Oldest House Museum and the Ernest Hemingway House Museum. Running 56 years in a row, the Key West House & Garden Tour has definitely earned its spot in any list of top things to do in Key West in December.

Key West New Year’s Eve Parties

Where: Various locations
When: December 31, 2016

Key West becomes crazy-fun on New Year’s Eve, with lots of lively parties happening all over town. If you decide to spend New Year at Key West, you can get your party on at these places:

  • The Dropping of the Conch Shell, to be held at Sloppy Joe’s Bar, where a giant, brightly lit conch shell is lowered from the roof of the bar at midnight, akin to the giant, glittering ball dropped at New York’s Time Square. This conch shell drop has been going on for 24 years.
  • The Lowering of the Pirate Wench, the New Year’s Eve special event at Schooner Wharf Bar. At close to midnight, Evalena Worthington, the titular Pirate Wench and co-owner of Schooner Wharf, will be lowered down the 75-foot mast of the schooner America 2.0 dressed in full pirate costume.
  • The New Year’s Eve Shoe Drop at Bourbon St. Pub. On New Year’s Eve, party with abandon with Key West’s LGBTQ community and watch drag queen Sushi get brought down from the pub’s roof cradled in a giant shoe reminiscent of the movie Priscilla Queen of the Desert.

Pick your own brand of crazy-fun and usher in the New Year partying Key West-style.

Your holiday in Key West, Florida is sure to be fun if you take part in these top things to do in Key West in December. So book your flight to the Florida Keys right now.

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Anna is a wandering writer. If she isn't wandering, she's working on other blogs. And if she's not doing that, either she's reading or she's busy with a crafting project.