There’s no more unique place to celebrate the season than Key West, where the holiday spirit thrives in unusual ways. After all, this is an island that prides itself on being “close to perfect and far from normal.”
During the month of December, the yuletide spirit of this Conch Republic kicks the fun up a few notches. So pack your swimsuit, your sunglasses, and suntan lotion and get ready to be merry in a bevy of festive new ways.
Get in the Spirit
Events kick off early in the month during the annual Hometown Holiday Parade on December 8, which features tropics-inspired floats, candy cane showers, Santas wearing swimsuits, and high-school bands marching to upbeat, festive renditions of holiday tunes. “Everybody comes out and lines the streets to watch the parade go by,” says Carol Shaughnessy, who’s lived on the island for 35 years. “It’s a wonderful way to connect with the locals.”
Another December must-do is to hop on a bicycle and cruise around the island taking in the incredible assortment of nautical holiday decorations. “Key West goes insane during the holidays in the best possible way,” Shaughnessy says. “We love decorating and we love getting dressed up, whether it’s us or our houses, so the holiday displays here are really over the top.” If you prefer being driven around, Old Town Trolley Tours and the Conch Tour Train company both offer nighttime tours through some of the most spectacular neighborhoods with holiday light displays.
Celebrate the Tropical Way
For a tropical twist on a holiday favorite, Nutcracker Key West (December 8–16) moves the story underwater, where the island’s famous shipwrecks take center stage and the mice are replaced by baby chickens and lively shrimp.
At the Truman Little White House, which was once the second home of President Harry S. Truman, presidential Christmas cards through the ages are on display, and the house itself is decorated with original decor from the building’s era.
At the iconic Custom House Museum, the annual Holiday Concert and Bazaar (December 19) features performances by local musicians and choirs, while local artisans sell unique, handmade fabrics, art, and jewelry. “It’s a great spot to find one-of-a-kind gifts,” says Shaughnessy.
On the water, the annual Schooner Wharf Bar Annual Lighted Boat Parade (December 15) is one of the island’s most popular traditions. Find a spot along the historic seaport to see everything from rowboats to historic schooners in all their holiday glory.
Afterward take in the one-of-a-kind nautical decor along the half-mile Harbor Walk of Lights. You’ll see Christmas trees made of lobster traps and fishing buoys, decked out palm trees, and sea life sculptures perfect for snapping selfies. Both The Reach Key West and Casa Marina Key West are within walking distance of the seaport, offering both luxury accommodations and easy access to all the festivities.
Ring in the New Year
Nobody does New Year’s Eve like Key West. At the iconic Schooner Wharf bar in the historic seaport, a pirate wench (who also happens to be the bar’s owner) drops from the top of a ship’s mast at midnight. At Sloppy Joe’s, the famous former haunt of Ernest Hemingway, a super-size conch shell drops from the roof. And for a truly unique experience, Key West celebrity drag queen Sushi steps into a giant red high-heeled shoe and drops from the balcony of the Bourbon Street Pub.
And if you’re staying in Marathon (about 1.5 hours from Key West), grab an early dinner then settle down at the beach with buckets of champagne and munchies with family, friends, and neighbors.
Colorful, kitschy, and fun, the Keys at Christmas is like no place else. While you’re in town celebrating, book a stay at a Hilton.