Things to Do in Key West During the Winter

Winter in Key West is a season unlike any other. The island transforms into a tropical holiday escape with mild temperatures, stunning ocean views, and a lineup of festive celebrations. The island’s laid-back yet festive atmosphere makes it a haven for those looking to celebrate the season uniquely and unforgettably. Whether you are discovering local shops along Duval Street or indulging in fresh seafood by the water, there is no shortage of winter things to do in Key West that make every moment unique.

Holiday Tours and Festive Activities

Holiday Sights and Festive Nights® Tour

Celebrate the season with the Holiday Sights and Festive Nights® Tour, a one-of-a-kind experience aboard Old Town Trolley. Guests can explore the island’s most beautifully decorated neighborhoods while enjoying complimentary cider and cookies. The tour includes special holiday light glasses, enhancing the twinkling displays along the route. 

This limited-time tour operates on select nights throughout December, offering a joyful way to embrace winter in Key West. The island’s historic streets, adorned with festive lights and unique holiday displays, make this a must-experience event for visitors looking to soak up the holiday magic in a tropical setting. Along the way, knowledgeable guides share fascinating stories about Key West’s holiday traditions and its charming past, making this tour both entertaining and informative. Each stop along the route adds a new layer of seasonal charm, ensuring that guests leave with memories of a warm and festive island experience. Taking part in this festive adventure is one of the most exciting Key West winter activities, unforgettably bringing holiday cheer.

Ghosts & Gravestones® Tour

For those who enjoy a mix of history and hauntings, the Ghosts & Gravestones® Tour provides a chilling look at the island’s supernatural past. This evening tour shares tales of Key West’s restless spirits and haunted sites, making it a spooktacular way to experience the island’s eerie side. A stop at the Key West Shipwreck Treasure Museum adds to the mystery, providing insight into shipwrecks and lost treasures. Available year-round, this tour offers a unique perspective during the winter months, blending history with seasonal intrigue. The cool winter evenings create the perfect atmosphere for uncovering Key West’s haunted past. The stories shared by the expert guides add an element of mystery and suspense, making this an unforgettable experience for those who dare to explore the darker side of winter in Key West. If you’re searching for thrilling winter things to do in Key West, this ghostly tour is an excellent choice.

Festive Parades and Celebrations

Lighted Boat Parade

One of the most spectacular Key West winter activities is the Lighted Boat Parade. Local boaters decorate their vessels with twinkling lights and festive displays, creating a dazzling spectacle on the water. The parade takes place in Key West Harbor, typically in mid-December, and is free for all to enjoy. Prime viewing locations include the Harbor Walk of Lights at the Historic Seaport, where guests can watch sailboats, fishing vessels, and luxury yachts glide by in a holiday procession. With holiday music playing in the background and the scent of salt in the air, this event captures the essence of winter things to do in Key West and offers a picturesque way to celebrate the season. The variety of vessels participating in the parade, from fishing boats to extravagant yachts, adds a unique and colorful display of creativity, making it a true spectacle for all ages. 

Hometown Holiday Parade

For a classic hometown celebration, the Hometown Holiday Parade showcases the charm and community spirit of winter in Key West. This family-friendly event features local bands, colorful floats, and an appearance by Santa Claus. The parade route runs along Truman Avenue and Duval Street, making it easy for visitors to find a perfect viewing spot. Held in early December, this festive tradition brings locals and tourists together in a joyful celebration of the season. Families line the streets with chairs, waving to performers and collecting candy as the parade makes its way through the heart of Key West. Local schools and businesses also participate, adding their creative flair to the floats, making this event a true reflection of the island’s close-knit community. The excitement and joy of the crowd create a heartwarming atmosphere, making this one of the best ways to kick off the holiday season in winter in Key West. The parade’s lively energy and entertaining performances leave spectators feeling festive and immersed in the holiday cheer. This event perfectly complements the other winter things to do in Key West, ensuring a well-rounded seasonal adventure.

New Year’s Eve Celebrations

New Year’s Eve in Key West is a celebration unlike any other, offering a mix of high-energy entertainment and laid-back island charm. The Conch Shell Drop at Sloppy Joe’s Bar and the famous Drag Queen Drop, featuring the drag queen Sushi at Bourbon St. Pub, are two of the night’s biggest highlights. These traditions attract visitors from across the country, creating a lively and unforgettable atmosphere. As midnight approaches, the island’s energy builds, with crowds gathering along Duval Street for music, drinks and anticipation of the new year’s arrival. Fireworks light up the sky over the water, providing a breathtaking backdrop for the festivities. No visit is complete without experiencing the electric atmosphere, which makes winter things to do in Key West truly unforgettable.

Those looking for a more refined experience can book a New Year’s Eve dinner cruise, where guests can enjoy gourmet meals, champagne toasts, and panoramic ocean views. For a more casual yet equally festive option, several bars and restaurants host themed parties featuring live bands, DJs and exclusive holiday menus. No matter how you choose to celebrate, winter things to do in Key West ensure a vibrant and unforgettable start to the new year. The variety of events and celebrations caters to all preferences, making New Year’s Eve in Key West a must-experience event for visitors. 

Seasonal Attractions and Experiences

Harbor Walk of Lights

The Historic Seaport transforms into a glowing holiday wonderland during the festive season. The Harbor Walk of Lights features illuminated palm trees, creatively decorated ships and a stunning 16-foot buoy tree that captures the island’s nautical spirit. The light displays stretch from the Ferry Terminal to Lazy Way Lane, creating a scenic and festive pathway that offers excellent photo opportunities. Taking in these breathtaking lights is one of the most picturesque winter things to do in Key West, especially for those who love holiday decorations and waterfront scenery.

Walking along the harbor, guests can take in the twinkling lights while listening to holiday music and sampling seasonal treats from vendors lining the route. Local artists and crafters also set up booths, offering unique gifts and souvenirs that reflect the island’s culture. Many waterfront restaurants participate in the celebrations, serving special holiday menus with fresh seafood, island-inspired cocktails and decadent desserts. For those looking to extend the experience, several companies offer guided holiday walking tours that share stories of winter in Key West while leading guests through the beautifully decorated areas. 

Historic Inn Tours

Key West’s historic inns and bed-and-breakfasts open their doors during December, inviting guests to step inside and experience the charm of the island’s architecture and holiday traditions. These tours provide a rare glimpse into some of the most beautifully preserved homes, each adorned with festive decorations and twinkling lights. Guests are often greeted with seasonal refreshments, such as warm cider or holiday-themed cocktails, adding to the inviting atmosphere.

Many of these inns date back to the 19th century, showcasing elegant furnishings, intricate woodwork, and lush tropical gardens that provide a stunning contrast to the winter season found in other parts of the country. Throughout these tours, visitors learn about the history of the homes and the people who once lived there, gaining a deeper appreciation for Key West’s cultural heritage. Some inns also feature live music, carolers, or local artisans showcasing handmade holiday gifts. Exploring these historic inns is one of the most intimate winter things to do in Key West, offering both nostalgia and seasonal charm.

For those who appreciate both history and holiday spirit, these tours offer a perfect way to explore Key West winter activities in a unique and memorable setting. The combination of stunning architecture, warm hospitality, and festive decorations makes this experience one of the most charming seasonal traditions in Key West. Whether you are staying at one of these historic inns or just visiting for the evening, the tour offers an intimate look at the island’s rich history and holiday cheer.

Final Thoughts

Winter in Key West is a season filled with experiences that highlight the island’s beauty, culture, and festive atmosphere. Key West winter activities blend tropical warmth with seasonal traditions, creating a getaway that feels both familiar and completely unique.

From the excitement of New Year’s Eve celebrations to the peaceful glow of the Harbor Walk of Lights, visitors will find plenty of winter things to do in Key West that make the holiday season truly special. The laid-back energy, combined with breathtaking views and rich traditions, ensures that every trip to Key West during the winter months is unforgettable. 

FAQs

What are the must-see holiday events in Key West during the winter?
The Lighted Boat Parade, Hometown Holiday Parade, Harbor Walk of Lights, and New Year’s Eve celebrations are among the most popular seasonal events in Key West. Visitors can also explore special seasonal tours and local festivities throughout December. These events showcase some of the best Key West winter activities and add to the island’s seasonal charm.

Are the holiday tours in Key West suitable for children?
Yes, tours like the Holiday Sights and Festive Nights® Tour and the Hometown Holiday Parade are family-friendly. The Ghosts & Gravestones® Tour may be better suited for older children and adults due to its spooky theme. Many of the light displays and seasonal events also provide a fun and engaging experience for kids of all ages, making them some of the best winter things to do in Key West for families.

When do the holiday light displays typically begin and end in Key West?
Most holiday light displays, including the Harbor Walk of Lights, begin in late November and remain illuminated through New Year’s Eve. Many decorations stay up through the first week of January, allowing visitors extra time to enjoy the festive ambiance. Strolling through these displays is one of the most breathtaking Key West winter activities that captures the essence of the season.

What is the weather like in Key West during the winter months?
Key West enjoys mild winter temperatures, typically ranging from the mid-60s to the mid-70s Fahrenheit, making it a perfect escape from colder climates. The weather is ideal for outdoor activities, from strolling along the beach to taking part in Key West winter activities like boat tours, sunset cruises, and festive events.