Christmas in Key West FL

If you're seeking a holiday season like no other, look no further than Christmas in Key West FL. Imagine twinkling lights wrapped around palm trees, Santa trading his sleigh for a jet ski, and tropical breezes replacing the winter chill. Key West transforms the holidays into a festive celebration filled with sunshine, charm, and island-inspired traditions.

Whether you're escaping the cold for your annual Key West getaway or looking for a unique Christmas adventure, this tropical paradise offers a holiday experience that blends classic traditions with quirky, tropical twists.

Things to Do in Key West at Christmas

Key West’s holiday events are as diverse and colorful as the island itself. From lighted boat parades to historic tours, here are the top things to do in Key West at Christmas:

1. The Harborwalk of Lights

Located at the Key West Historic Seaport, the Harborwalk of Lights illuminates the waterfront with over 60,000 lights. Palm trees, nautical-themed Christmas trees, and buoy decorations light up the night sky, creating a stunning holiday display. The event runs throughout the entire month of December, so visitors can enjoy the festive atmosphere all month long.

A notable feature of this annual event is the lobster trap Christmas tree, a tribute to the island’s rich maritime history. Decorated with lights, the lobster trap tree is an Instagram-worthy spectacle that you will not want to miss. Walk along the seaport, grab a drink at one of the nearby bars, and take in the unique blend of Key West’s nautical charm and holiday spirit.

2. Schooner Wharf Bar Lighted Boat Parade

On December 14th, locals and visitors gather for the annual Schooner Wharf Bar Lighted Boat Parade, where dozens of boats adorned with christmas lights, sail through the Key West Bight. Whether you watch from the Harborwalk or hop aboard a boat for a closer view, this event is a must-see for anyone spending Christmas in Key West.

Each year, participants go all out to show off creative holiday displays on their boats, from whimsical holiday-themed designs to elaborate light shows. If you're watching from shore, be sure to arrive early to secure a good viewing spot. The event typically draws large crowds, so finding a prime location along the waterfront is key to enjoying the full experience.

For those interested in being part of the action, many boat charters and tour companies offer parade-viewing cruises, giving you an up-close and personal view of the illuminated vessels. You can enjoy the festive sights while sipping a cocktail and cruising through the harbor—a truly unique holiday experience.

3. Holiday Historic Inns Tour

Explore the rich history of Key West during the Holiday Historic Inns Tour, where you'll visit beautifully decorated bed-and-breakfasts and historic homes. On this tour, you’ll enjoy festive lights, live music, and delicious refreshments. This charming holiday tradition gives you a taste of both Key West’s architectural history and its holiday spirit.

Participating inns include some of the island’s most iconic properties, such as The Mermaid & The Alligator, Island City House, and The Gardens Hotel. Each stop on the tour offers guests a glimpse into the island's past, with innkeepers sharing stories about the history of their homes. In addition to learning about the island’s rich heritage, visitors can indulge in complimentary holiday treats and cocktails at each location.

4. The Nutcracker Key West

For a fun twist on the classic Christmas tale, don't miss the Conch Republic version of The Nutcracker. This performance features everything from roosters to conch shells, offering an island-inspired take on the beloved ballet. It’s a magical experience that will leave you captivated by the creativity and charm of the local performers.

Performed biannually, The Nutcracker Key West showcases the island's creative spirit, blending traditional ballet with local flair. The production includes elaborate sets featuring sea fans, anemones, and other tropical elements that transport audiences to an underwater wonderland. Whether you're a ballet aficionado or a first-time viewer, this unique performance is a holiday must-see.

Unique Holiday Experiences in Key West

Christmas in Key West isn’t just about festive lights and traditional events—it’s also an opportunity to enjoy unique island experiences. Here are a few more offbeat holiday activities to make your Christmas unforgettable:

5. Key West Lighted Bike Parade

Join the annual Lighted Bike Parade in Bayview Park, where locals decorate their bikes with lights and holiday ornaments, creating a moving display of holiday cheer. The parade benefits local charities and adds a bit of fun to the holiday season.

The Lighted Bike Parade is more than just a fun ride through town—it’s an important event for the local community, as it supports a holiday toy drive for families in need. Participants are encouraged to deck out their bikes with as many lights and decorations as possible, creating a festive and colorful spectacle. This event brings the entire community together, and it’s a great way to get into the holiday spirit while giving back to those in need.

6. Dolphin Watch and Snorkeling Tours

Escape the holiday rush with a dolphin watch tour, or dive into the crystal-clear waters of Key West on a snorkeling adventure. See marine life up close and enjoy the island's natural beauty, all while celebrating the holidays in a way that only Key West can offer.

Key West’s waters are home to playful dolphins, and dolphin watch tours provide a unique opportunity to see these incredible creatures in their natural habitat. Many tours also include a snorkeling stop, where you can explore the colorful coral reefs and vibrant marine life that surround the island. It’s a fantastic way to enjoy the outdoors and take a break from the hustle and bustle of holiday shopping and festivities.

7. New Year's Eve in Key West

If you’re staying through New Year’s Eve, be sure to witness the Lowering of the Pirate Wench. At midnight, the pirate wench is lowered from the mast of the Schooner America 2.0 while the crowd cheers, fireworks burst in the sky, and live music fills the air. It’s a New Year’s Eve tradition that only Key West could dream up.

For those looking for something a bit more traditional, Key West also hosts a variety of other New Year’s Eve celebrations, including the famous Conch Shell Drop at Sloppy Joe’s Bar and the Red Shoe Drop at the Bourbon Street Pub, where a drag queen descends in a giant red high heel. No matter how you choose to ring in the new year, Key West offers a variety of fun and quirky options that are sure to make your celebration unforgettable.

Year-Round Activities During the Holidays

The holiday season may be filled with festivities, but the island’s natural beauty and charm remain a draw year-round. Here are a few activities to enjoy while you’re in Key West this Christmas:

• Day Trip to Dry Tortugas National Park: Take a boat or seaplane to this remote island park, home to Fort Jefferson and some of the best snorkeling spots in North America. The park’s pristine waters and abundant marine life make it a popular destination for nature lovers and adventure seekers.
• Parasailing Adventures: Get a bird’s-eye view of Key West as you soar high above the water on a parasailing adventure. The island’s turquoise waters and stunning coastline are even more breathtaking from above.
• Mallory Square Sunset Celebration: A Key West tradition, the Mallory Square Sunset Celebration features live performances, local vendors, and a front-row seat to one of the most beautiful sunsets in the world. Each evening, as the sun sets over the Gulf of Mexico, locals and visitors gather to watch the sky light up in shades of pink, orange, and purple. It’s a magical way to end a day of holiday festivities.

Where to Stay in Key West During Christmas

When planning your holiday getaway, Historic Key West Vacation Rentals is the ideal place to stay. Our luxury vacation rentals offer all the comforts of home, along with the unique charm of Key West’s historic architecture. Whether you’re looking for a cozy cottage for two or a spacious estate for the whole family, our vacation specialists can help you find the perfect rental for your stay.

Our properties are located throughout the island, putting you within walking distance of the best holiday events and attractions. Whether you want to be near the Historic Seaport, Duval Street, or Mallory Square, we have a rental that will suit your needs. Plus, with fully equipped kitchens and private outdoor spaces, you can enjoy a relaxing holiday retreat without sacrificing any of the comforts of home.

Your Perfect Christmas in Key West FL Awaits

From festive light displays to one-of-a-kind holiday traditions, Christmas in Key West FL offers an unforgettable holiday experience. Whether you’re participating in a lighted boat parade, watching the sunset from Mallory Square, or simply soaking in the island’s tropical charm, Christmas in Key West is sure to be a holiday vacation you will remember forever.

Ready to book your Christmas Day getaway? Contact Historic Key West Vacation Rentals today and start planning your tropical holiday escape!