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.

Book tickets early for Key West's tropical version of the Nutcracker ballet at Tennessee Williams Fine Arts Center. Presented every other year, the tale of young Clara's dreamlike visit to the land of the Sugarplum Fairy is transformed into an...  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

You won't find better seats for two of Key West's best holiday celebrations--the Lighted Boat Parade and New Year's Eve at Schooner Wharf--than aboard the America 2.0. This sleek schooner is a near replica of the first boat to win the America's...  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 Train Holiday Lights Tour is one of the easiest ways to take in the elaborate trimmings draped across the historic homes and inns. The tour makes many a top 10 list for good reason. Their bright yellow trains have been winding the...  Read More

The Little White House house is a living museum that has been impeccably restored and is a sight to behold during the holidays. It's decorated exactly as it was in World War II right down to the Christmas tree lights and their collection of...  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 three Christmas trees--one made with fishing buoys, another made with...  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 (305-293-9800), a disco party...  Read More

As holiday parades roll down Main Street in small towns across America, Key West residents string garlands and lights on everything from dinghies to mega-yachts and take their festivities to the water. At Key West's annual Lighted Boat Parade in...  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