A Guide to the Holiday Season in Key West
If your idea of a white Christmas is more white sand beaches and less snow, head to Key West this holiday season. Here you can escape the winter chill without missing out on the season’s festivities. Trade your sweaters for swimsuits and add a little vitamin D to your holiday cheer.
From where to stay to the best places on the island to explore, shop, and feel merry, here’s your holiday guide to visiting Key West.
COAST is Clear Music & Arts Festival | December 1-4
This year, December kicks off with four days of live music in Key West. The festival takes place across several legendary local venues — i.e. the San Carlos Institute, Green Parrot, and Blue Heaven. It’s a great opportunity for travelers to get in touch with the local music scene. Some of the critically-acclaimed headliners include Shakey Graves from Austin, Preservation Hall Jazz Band from New Orleans, and Fruit Bats from Chicago.
Coast is Clear Music & Arts Festival. Key West, FL
6th Annual Holiday Concert & Bazaar | December 9, 5-9 pm
Find local gems and one-of-a-kind gifts for your family and friends at the opulent Holiday Bazaar. Featuring some of Key West’s finest artisans, food and libations, the event offers shoppers a wide variety of troves. Choose from handcrafted jewelry, clothing, textiles, home decor, and more.
The entertainment portion of the evening will feature music from local bands and choirs, as well as a holiday light show that will be projected on the face of Custom House — where the event takes place.
6th Annual Holiday Concert & Bazaar. Custom House. 281 Front St. Key West, FL
Nutcracker Key West | December 11
This production is the largest community stage performance in Key West. Celebrate the holidays in classic style by taking in this rendition of Nutcracker. The show features 60 local performers (children and adults) and 15 professional dancers. The production takes place at the Tennessee Williams Theatre, a beautiful space and tribute to one of the area’s most well-known former resident playwrights.
Nutcracker Key West. Tennessee Williams Theatre. Key West, FL
31st Annual Schooner Wharf Bar Lighted Boat Parade | December 11
The lighted boat parade is one of the most quintessentially Key West holiday traditions. This year’s parade will begin at 8 pm, however, the festivities will begin at 6 pm with a performance by the Bahama Village Steel Pan Band followed by holiday tunes by local musicians.
The parade begins in the Historic Seaport, then passes in front of the Schooner Wharf Bar and the judge’s stand. Instead of traditional floats, this parade features boats decked out in their holiday best.
31st Annual Schooner Wharf Bar Lighted Boat Parade. Schooner Wharf. Key West. FL
Shopping in Key West
From artisan stands at events like the Holiday Concert Bazaar to art galleries to local establishments, there are a lot of options for shoppers seeking holiday gifts while in town. For those with vintage taste, the Clinton Square Market in The Shops at Mallory Square features great trinkets, jewelry, and souvenirs. Some more unique shopping destinations include the Key West Sponge Market, Key West Shells & Gifts, and The Southernmost Gift Shop in Key West.
Holiday Hotel & Villas
Reservations for hotel stays in Key West during this year’s holiday season are filling up. Book your stay at least 21 days in advance and save up to 20% on all room types at Parrot Key Hotel & Villas.
