Christmas in the Keys

Christmas in the Keys

Christmas in the Florida Keys is a magical experienced that combines the festive spirit of the holiday season with the laid-back, tropical vibes of the Keys. While the Keys may not have the traditional winter wonderland scenery, they make up for it with their own special charm. We will highlight some of our favorite festive things to do while spending the holidays in the Keys. 

Lighted Boat Parades

One of the highlights of Christmas in the Keys is the annual "Boat Parade". Instead of snow covered streets, you'll find boats of all sizes decked out in colorful lights and decorations, parading through the waterways.  It's a sight to behold as these festive vessels glide along, spreading holiday cheer to onlookers. There are boat parades held in Key West, Stock Island, Key Colony Beach, and Key Largo.  If you are in the Keys during the holidays, this is a must do! 

Holiday Historic Inn Tour

This is our favorite holiday tour to do annually!  The Holiday Historic Inn Tour is a festive and enchanting experience that takes you on a journey through the rich history and charm of Key West's historic inns during the holiday season. The tour takes place in December when the inns are adorned with holiday decorations, twinkling lights, and extravagant Christmas themed displays.  

Throughout the tour, you have the opportunity to enjoy complimentary treats and beverages for a change to indulge in the flavors of the season while immersing yourself in the history & charm of Key West.  At each inn there will be different offerings of wine, cocktails, non alcoholic beverages, appetizers, deserts, hors d'oeuvres and more! The Holiday Historic Inn Tour is not only a visual feast, but also a feast for your tastebuds. 

Key West Annual Holiday Parade

 

This festive parade takes place in December and is a highlight of the holiday season in Key West. The parade is in the heart of Old Town Key West, filling the streets with colorful floats, marching bands, local organizations and enthusiastic spectators. It begins in the late afternoon, just as the sun starts to set, creating a magical tropical atmosphere as the streets are illuminated with twinkling lights and holiday decorations.

The parade route winds through the historic streets of Key West, passing iconic landmarks and charming neighborhoods. Whether you're a local or a visitor, this parade is a must see event that captures the essence of the holiday season in the Florida Keys.  

Holiday Village & BeLighted Bike Ride

Decorate your bikes and join the “Best Bike Contest” that accompanies the BeLights Bike Ride. It's quite the event seeing all of the elaborately decorated bicycles! The The bike ride will begin at 8pm starting at the Coffee Butler Amphitheater and follow the same route as the Fantasy Fest Parade, Whitehead to Duval St. 

The Annual Islamorada Chamber of Commerce Holiday Fest usually takes place in early December, on the Great Lawn at Founders Park. Bundle up for one of the most exciting community events of the season, it is a great time for everyone to kick off the holiday season.

The event’s star attraction, the Holiday Fest Snow Mountain, will be made out of 30 tons of SNOW! More than enough to delight winter-clad children and adults alike. Meanwhile, throughout the evening, Islamorada’s 35-foot high official holiday tree will be blowing magical snow through its branches. 

Snow is not all there is at Holiday Fest! The Holiday Parade will kick off with floats, antique cars and, of course, Santa himself. The festival also offers the unique Holiday Gift Bazaar, perfect for getting the shopping season started right. A popular feature of the Bazaar is the online auction of handcrafted ornaments.

 

Old Town Trolley Holiday Nights & Festive Sights 

The Old Town Trolleys are a classic way to see Key West. For the holidays, the popular green and orange cars are decorated with holiday lights and take you through the best-decorated neighborhoods on the island. See how the island transforms for the holidays with a guided tour leaving from the iconic Mallory Square Key West.

No need to gas-up the snowblower this year if you’re planning a holiday escape to the Florida Keys! Here, Christmas chill’ means rockin’ your flip-flops and kicking back island-style! One of the best ways to do that is hopping a ride on Old Town Trolley’s Holiday Sights & Festive Nights Tour! The Southernmost City is all a twinkle, as the locals decorate their historic Key West homes in a splendid cascade of lights and other decorative touches to see who can outdo the other in a friendly, holiday-inspired competition. Enjoy cookies, cider and a 60-minute Key West tour that is sure to put you in the holiday spirit. 

 

Key West “Bight” before Christmas® Celebration

A Nautical theme honoring the maritime history of the Key West waterfront.  The Key West “Harbor Walk of Lights” traditional main features will light up that night, including the 20’ Fishing Buoy Tree, a 16’ Nautical Christmas Tree and the original Key West Lobster Trap Tree. 

Stroll along the water’s edge for a merry infusion of colorful lights and nautical holiday displays. See light sculptures of ship’s anchors, tropical birds, tropical fish, a flock of pink flamingos, jolly pelicans, merry manatees, animated sea turtles and dancing dolphins, and even a festive moray eel, all under brightly lit holiday palm trees! And with 3 blocks of sparkling holiday lights and displays around the Key West Bight Marina and Historic Seaport, the Key West “Harbor Walk of Lights” is destined to bring miles of holiday smiles to our visitors and locals alike.   

The “Harbor Walk of Lights” stretches along the seawall past Greene St, William St, and Margaret St. to the K.W. Ferry Terminal. Don't miss it! It's nightly throughout the holiday season and one of our favorite things to do!