Key West, Florida, is more than just a sunny paradise; it transforms into a festive wonderland during the holiday season, bursting with activities and events that capture the spirit of Christmas. From ice skating and holiday lights to unique Christmas parades and enchanting performances, Key West offers a magical experience unlike any other. In this guide, we will explore the best things to do in Key West at Christmas, including renowned Key West holiday events and the charm of our Key West vacation rentals.
Whether you’re a local or visiting for the season, there’s no shortage of festive fun in this island paradise.
Waterfront Winter Wonderland
From December 15th to December 30th, Key West Vacation Homes is proud to sponsor the Waterfront Winter Wonderland event at the Coffee Butler Amphitheater in Truman Waterfront Park. This December, the space transforms into a winter wonderland, inviting families and individuals of all ages to partake in holiday merriment amidst a tropical setting. The event features an ice skating rink, various games, rides, attractions, music, and a spectacular display of lights. For those looking to indulge in holiday shopping, the amphitheater’s vendor village offers a plethora of shopping opportunities with multiple food stalls and local artisan crafts. Themed skate nights, live performances, and festive celebrations occur throughout the season, adding to the holiday delight. Your children can enjoy rides like carousels, swings, and slides with a $10 all-you-can-ride wristband. Don’t miss out on special holiday experiences, such as photo opportunities with Santa, holiday crafts, and much more. Admission is $10 per person with free entry for children aged five and under. You can enjoy a one-hour ice skating session for an additional $20 per person, making it a day filled with joy and laughter.
Shopping at Mallory Square
Christmas in Key West is not complete without a shopping spree at Mallory Square. On December 17th, Santa Claus trades snow for sunshine, making a grand appearance from 12:00 p.m. to 2:00 p.m. Families can capture memorable moments with Jolly St. Nicholas and drop off Christmas letters in Santa’s mailbox. At The Shops at Mallory Square, you’ll find a variety of stores offering unique gifts and souvenirs. From Cuban Coffee Queen to Key West Pottery and Whit’s Frozen Custard, there’s something for everyone. Other notable shops include Backyards of Key West, Native Colors, Damon Designs, Aqua D’ Keys, Twisted Tinsel, and Southernmost Arcades. Whether you’re looking for handcrafted jewelry, fine art, or quirky souvenirs, Mallory Square provides an exceptional shopping experience during the holidays.
Key West Christmas Parade
One of the best things to do in Key West at Christmas is to attend the annual Key West Christmas Parade. On December 3rd, the holiday spirit parades down beloved Duval Street, marking the beginning of the festive season. Civic leaders, local churches, and community groups put on a magnificent display of floats and decorations, spreading cheer throughout Old Town. The parade starts at Truman and White streets at 7:00 p.m., proceeds down Truman to Duval, and ends at Caroline Street. Approximately 50 entries participate each year, and it concludes with Santa and Mrs. Claus. The energy and excitement surrounding the parade are infectious, capturing the essence of what makes the holiday season in the Keys so special.
See the Harbor Walk of Lights
One of the top things to do in Key West, Florida, during the whole month of December is to see the Harbor Walk of Lights. This enchanting event begins as the lights come on at 6:00 p.m., with holiday music starting at 5:00 p.m. The best views can be found at Harbor Walk plaza at Greene and Elizabeth Streets. The walk features creative holiday displays and thousands of lights, celebrating the “Maritime History of Key West.” Highlights include the 20’ Fishing Buoy Tree, a 16’ Nautical Christmas Tree, and the original Key West Lobster Trap Tree. Light sculptures include anchors, tropical birds, fish, flamingos, pelicans, manatees, sea turtles, dolphins, and even a festive moray eel—all under brightly lit palm trees. The three blocks of sparkling lights and displays around the Key West Bight Marina and Historic Seaport make this a not-to-be-missed holiday tradition.
Watch the Nutcracker Key West
For those looking for a unique holiday show, Nutcracker Key West is a captivating reimagining of the classic holiday ballet. Running from December 5th to December 15th at the Tennessee Williams Theatre, this show infuses the vibrant spirit and rich history of the Florida Keys into the traditional ballet. Joyce Stahl, a classically trained dancer, envisioned a production that would capture Key West’s distinct character, celebrating its maritime heritage, natural beauty, and eccentric charm. The performance delights audiences with sugarplum fairies trading tutus for sea fans, and the battle between mice and soldiers taking on a tropical twist. It’s a marvelous blend of art, music, and local flair, perfect for the entire family.
Eaton Street Christmas Stroll
On December 10th, Eaton Street transforms into the southernmost North Pole. From 3:30 p.m. to 7:30 p.m., visitors can wander the blocks between Whitehead and Simonton, stopping at various venues like Williams Hall for a concert from the Bahama Village Music Program. Enjoy classic cartoons at Tropic Cinema, festive cocktails at The Studios, and a traditional Christmas concert at St. Paul’s. The Studios of Key West hosts an open house during the evening, allowing visitors to check out the members’ winter exhibition or enjoy cocktails on the rooftop at sunset. The Eaton Street Christmas Stroll is an evening of music, art, and festive cheer, making it a must-visit event during the holiday season in Key West.
Take the Conch Tour Train Holiday Lights Tour
A tradition since the 1950s, the Conch Tour Train offers a special Holiday Lights Tour from December 8th to December 23rd. Before boarding, guests can indulge in cookies and warm cider while prepping for some festive caroling. Once on board, the train cruises through Key West, showcasing the stunning holiday lights adorning the streets, businesses, and homes. One unique feature of this tour is the special glasses provided to enhance the light show, elevating the experience to new dazzling levels. It’s a magical ride that lights up the night and spreads holiday cheer for all to enjoy.
Plan Your Key West Vacation!
Are you ready to start planning your holiday adventure in Key West? Browse our selection of waterfront Key West rentals today and find the perfect match for your stay!
Stay with Key West Vacation Homes
When planning your visit to Key West during the holiday season, consider staying with Key West Vacation Homes. These rentals offer all the comforts of home while situating you close to all the exciting holiday events and activities. Immerse yourself in the local culture, enjoy the festive cheer, and create unforgettable memories with family and friends. Key West transforms into a festive paradise come December, offering visitors a plethora of holiday activities and events. Whether shopping at Mallory Square, attending the Key West Christmas Parade, or enjoying a performance of Nutcracker Key West, you’ll find the best things to do in Key West at Christmas. And with comfortable Key West vacation rentals from Key West Vacation Homes, your holiday stay will be as magical as the island itself.
