Experiencing The Southernmost Holidays in the USA

There are few destinations as sun-soaked and festive as Key West, Florida, which is why it’s an ideal place to travel during the holiday season. We take our celebrations out on the water in true local fashion with a lighted boat parade. We do offer our best local gifts for traveling shoppers at a local artisan market, and we boogie down at a number of concerts, shows, and festivals. 

For some more specific insights, here’s our guide to experiencing the southernmost holidays in the United States of America. 

Schooner Wharf 29th Annual Key West Lighted Boat Parade

December 14th

Anyone who is in town on the night of the 14th will want to head over to Schooner Wharf to catch the annual lighted boat parade party. Each year, travelers and locals line up along the Harborwalk of Lights to enjoy a procession of boats decked out in colorful Christmas lights coast along the water. This one-of-a-kind party takes place right in the heart of Key West’s historic Seaport. 

In addition to the vibrant attractions, there will also be complimentary drinks and hors d’oeuvres, and contests for the most impressively decorated ships. You can expect some strong efforts from participants, as there will be over $20,000 in prizes awarded to the top 12 vessels chosen by judges. 

Schooner Wharf 29th Annual Key West Lighted Boat Parade. Key West, FL 

Key West Artisan Market

Throughout December

From November 4th until April 4th, the Key West Artisan Market pops up weekly at Key West’s beloved Higgs Beach. The market comes together every other Sunday, and it features eats provided by local restaurants, island art, clothes, home accessories, and a whole lot more. The open-air bazaar is a favorite among local and traveling shoppers in Key West, which is why it’s a must-visit during the holiday season.

Whether you’re perusing unique conch shells, inspired island jewelry, or unique paintings created by an artist nearby—you’ll be sure to find some special gifts here. In addition to all of the holiday shopping that one can enjoy at the Key West Artisan Market, guests can also enjoy artist readings, live painting, and music. 

Key West Artisan Market. Key West, FL 

Conch Republic Seafood Company Holiday Classic Car Show

December 15th

Car lovers and travelers will have another great time this year at the annual Conch Republic Seafood Company Car Show. Showcasing a stellar lineup of classic automobiles, the car owner’s will decorate each vehicle with vibrant holiday swag. There will also be a contest for the best engine, interior, and original custom car details. On top of it all, the judges will crown a best in show, and the fans will choose a “people’s choice” winner. 

This promises to be a fun-filled day, and an easy attraction for travelers hanging around the island. If you feel like giving back this holiday season, then the Conch Republic Seafood Company Holiday Classic Car Show invites you to bring an unwrapped toy for donation to the Monroe County Domestic Abuse Shelter

Conch Republic Seafood Company Holiday Classic Car Show. Key West, FL 

Key West Holiday Concert & Bazaar

December 18th

Holiday season travelers coming to Key West this December can check out a great time at the annual Key West Holiday Concert & Bazaar. The fourth annual event from the Key West Art & Historical Society will take place on a Wednesday evening on the gorgeous sweeping porch of the historic Custom House in Key West. 

In addition to live music, there will be food and drinks provided by local chefs and bartenders. You can also shop for unique gift options here like locally produced art, clothes, and funky jewelry. 

Key West Holiday Concert & Bazaar. Key West, FL 


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