Yuletide Spirit with a Twist: Key West's 10 Best Holiday Attractions

While it may seem counter-intuitive to head to a tropical locale to catch the holiday spirit, Key West in December is a wonderland of festive surprises. The warm temps might very well be the reason residents approach the yuletide season with such unbridled enthusiasm. Visitors can enjoy a bevy of merry events and attractions throughout the month. 

The historic Old Town architecture takes on a new glow, as the gingerbread millwork is laced with twinkling lights and icicles. Giant snowflakes hang from wraparound balconies, and red ribbons and green garland stripe the columns. Candy canes, penguins and snowmen mix with the bougainvillea, frangipani and hibiscus along the lawns. The Holiday Lights Conch Train Tour, Holiday Historic Inn Tour--or even just cruising around on a bike--are  great ways to see the decorations.

The Historic Seaport plays host to a series of events as part of their Bight Before Christmas celebration. This includes the Nautical Harbor Walk of Lights and the Key West Lighted Boat Parade. Festivities culminate in an island-wide New Year’s Eve Celebration where various bars drop things way more interesting than a crystal ball. Think pirate wench, giant conch shell, and even a drag queen inside a red super-sized, high-heel shoe. For a full calendar of events, visit the Key West Holiday Fest website.

Named after the Key's "other" famous writer-in-residence, the Tennessee Williams Fine Arts Center is home to the South Florida Symphony. Nationally recognized conductor Sebrina Maria Alfonso brings together eminent musicians from around the...  Read More

Cruising Old Town Key West by bicycle is one of the best ways to enjoy the whimsical holiday decorations. Traditional architectural details are transformed, as gingerbread millwork is laced with twinkling lights and icicles. Giant stars and...  Read More

Their schooner, America 2.0, is a near replica of the first boat to win the America's Cup in 1851 with teak decks and mahogany trimmings. When the engines turn off, guests witness the power of the wind and the talent of the crew. They offer...  Read More

Sebago Watersports
Photo courtesy of Schooner Appledore II

How would you like to actually be on one of the vessels in the Key West Lighted Boat Parade? You can participate in the action aboard Sebago's Schooner Appledore II, a traditional sailing vessel built by the Harvey Gamage Shipyard in South...  Read More

The Conch Tour Train makes a lot of top 10 lists for good reason. Their bright yellow trains have been winding the shady streets of Old Town since 1958. Normally the tour is a pretty straightforward rundown of the local sights and rich island...  Read More

Key West has served as a presidential retreat since 1880 when Ulysses S. Grant visited the island. This house belonged to Harry Truman and his wife Bess. Truman reportedly despised living in Washington and viewed this as his sanctuary. He spent...  Read More

Despite being so far away from the North Pole, the inns in Key West are decorated for the holidays as if they were expecting Santa as a guest. Revel in that holiday spirit--and Key West's unique architecture and heritage--during the Holiday...  Read More

The holiday season in Key West kicks off each November with the "Bight" before Christmas festivities along the Historic Seaport. The Nautical Harbor Walk of Lights includes a trap float Christmas tree, a fresh pine nautical Christmas tree and a...  Read More

Ring in the New Year in the Florida Keys where you can enjoy balmy temps and a variety of celebrations where they'll be "dropping" things way more interesting than a crystal ball. In front of the Bourbon Street Pub, a disco party goes non-stop...  Read More

As holiday parades roll down Main Street in small towns across America, the residents of Key West are stringing garlands and lights on everything from dinghies to mega-yachts and taking their festivities to the water. At Key West's annual...  Read More


Meet Claudia Miller

Claudia Miller has been writing about South Florida for over 17 years--seven from Key Largo. A budding photographer, she can usually be found stalking a sunset. Despite being a tad...  More About Claudia

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