Christmas Events in Key West

Your Guide to a Tropical Holiday Celebration

If you're searching for a tropical twist to your holiday season, look no further than Key West. With its warm weather, festive lights, and unique island charm, Key West is the perfect escape from traditional snowy winters and the setting for a very special holiday. This island paradise transforms into a magical wonderland of Christmas events and activities that will make your holiday unforgettable. You’ll want to book your stay at Historic Key West Vacation Rentals for the ultimate experience.

Why Celebrate Christmas in Key West?

Key West’s average winter temperature of 75 degrees offers a sunny escape, perfect for trading snow for sand. Whether you’re looking to lounge on the beach or explore a festive holiday scene, this island offers something for everyone. Imagine celebrating the holidays surrounded by twinkling lights on palm trees, colorful boat parades, and outdoor events – all in flip-flops.

Top Christmas Events in Key West

Key West knows how to throw a party, and Christmas is no exception. The island hosts a variety of unique events, blending traditional holiday spirit with a tropical twist. Here’s a look at some of the must-see Key West events to plan your holiday getaway:

1. Lighted Boat Parade

The annual Key West Lighted Boat Parade is a holiday spectacle like no other. Imagine the beauty of dozens of boats gliding across the water, each adorned with thousands of twinkling lights and creative holiday decorations. Sailboats, yachts, and even fishing boats get in on the action, making this event a highlight of the Key West holiday season. Participants go all out, often decorating their boats with light displays such as Santa’s sleigh, Christmas trees, or tropical holiday scenes.

The best viewing spots are along the Historic Seaport or Mallory Square, where spectators gather early to secure prime spots for watching the parade. Many local bars and restaurants offer special viewing areas with food and drink packages, making it easy to enjoy the show with a festive beverage in hand. This year’s Lighted Boat Parade will be held on December 9, so don’t miss out on this magical event that perfectly captures the spirit of a Key West Christmas.

2. Holiday Historic Inn Tour

For a taste of Key West's rich history and holiday cheer, don't miss the Holiday Historic Inn Tour. This event allows visitors to tour some of the island’s most charming and historic inns, each beautifully decorated for the season. The inns are dressed up in their holiday best, with garlands, lights, and ornaments, providing a festive backdrop as you tour these architectural gems.

On the tour, you’ll get a behind-the-scenes look at Key West’s famous bed-and-breakfasts and boutique inns, many of which date back to the 19th century. Each inn offers something special during the tour, such as holiday music, hors d'oeuvres, and festive drinks.

This is also a great opportunity to discover some of the island’s hidden treasures and maybe even book a stay for your next visit! The 2024 Holiday Historic Inn Tour will take place on two nights—December 9 and December 16. Tickets tend to sell out quickly, so be sure to reserve your spot in advance.

3. Key West Holiday Parade

The Key West Holiday Parade is a family-friendly event that brings the community together in a joyful celebration of the season. Held on December 7 this year, the parade kicks off in Bayview Park and makes its way through Old Town, traveling along Truman Avenue and Duval Street. The streets are lined with spectators eagerly awaiting the arrival of festive floats, marching bands, and local performers.

One of the unique features of the Key West Holiday Parade is the island’s creative flair. You’ll see floats decorated with a tropical twist—think Santa Claus arriving on a boat or palm trees wrapped in lights. Local businesses, schools, and community organizations all take part, adding to the festive atmosphere.

Kids will especially love the holiday-themed costumes and the chance to catch candy from the parade participants. Whether you're visiting with family or enjoying the parade solo, this is one event that captures the true spirit of the holidays in Key West.

4. The Schooner Wharf Bar Lighted Boat Parade

Key West takes boat parades seriously, and the Schooner Wharf Bar Lighted Boat Parade is one of the most popular events of the holiday season. Picture a parade of boats, large and small, cruising through the Key West Harbor, all illuminated with holiday lights. What makes this event stand out is the variety of vessels—from elegant schooners to humble dinghies, all decorated with incredible attention to detail. You’ll see boats with reindeer on deck, Santa at the helm, and plenty of holiday lights reflecting off the water.

The parade is held at Schooner Wharf Bar, where you can enjoy live music, holiday-themed drinks, and the best view of the event. Prizes are awarded for the most creative holiday displays and well-decorated boats, so expect some truly impressive displays.

If you want to make the most of this event, consider reserving a seat at one of the waterfront bars or restaurants offering prime viewing spots. The 2024 Schooner Wharf Bar Lighted Boat Parade will be held on December 12, 14, & 15.

Indulge in Island Flavors During the Holidays

No Christmas celebration in Key West would be complete without indulging in the island’s delicious culinary scene. During the holidays, many local restaurants offer special Christmas menus featuring fresh seafood, tropical cocktails, and island-inspired holiday dishes. Imagine trading in your traditional holiday turkey and mashed potatoes for a seafood feast of stone crab, lobster, and conch fritters.

For a true Key West dining experience, make reservations at one of the island’s top-rated restaurants, many of which feature live music and holiday-themed décor. From fine dining to casual beachside eateries, Key West has something for everyone. Don’t miss out on trying local favorites like Key lime pie for dessert or a holiday cocktail infused with the flavors of the tropics.

Where to Stay in Key West for the Holidays

If you’re planning a trip to Key West this holiday season, staying in a vacation rental offers the ultimate experience. Whether you’re seeking a romantic escape for two or a family-friendly getaway, Historic Key West Vacation Rentals offers a wide range of vacation rentals to suit your needs. Choose from cozy cottages, luxury homes, and everything in between. Plus, you can take advantage of their concierge services to help you plan the perfect holiday itinerary.

For more details on the best places to stay during the holiday season, check out the wide range of Key West vacation rentals to find the perfect home for your festive getaway.

Plan Your Perfect Key West Christmas

From festive events to warm weather, Key West is the ideal destination for a tropical Christmas celebration. Be sure to book your stay with Historic Key West Vacation Rentals and experience the magic of the holidays in paradise. Whether you're exploring the Lighted Boat Parade, touring historic inns, or simply enjoying the island's laid-back vibe, you're guaranteed a holiday season to remember.