Key West is the perfect holiday destination with the sun always shining, the waters stay inviting all year round, and festivity reigns no matter the season.

Whether you’re looking to soak in the holiday cheer or simply unwind, Key West offers a plethora of festive activities and events that promise to make your holiday season unforgettable.

This guide will dive into the Christmas events in Key West, the best things to do in Key West, and more so your holiday plans can be as bright as the Key West sunshine. After days of exploring all the Key West festive activities, relax and rejuvenate at one of our incredible Key West vacation rentals.

Key West Events for the Holidays

Waterfront Winter Wonderland

This December, the Coffee Butler Amphitheater at the Truman Waterfront Park will transform into a Key West Winter Wonderland for a family-friendly holiday experience. Imagine ice-skating in the Key West air, surrounded by enchanting light displays, games, rides, and more. The amphitheater’s vendor village offers a variety of delicious food options and unique local artisan products perfect for holiday shopping. At the Waterfront Winter Wonderland, you can enjoy rides like carousels, swings, and slides. Come for the photo opportunities, letters to Santa, and festive crafts that complete the experience. The ice rink allows both seasoned skaters and beginners to glide gracefully and create lasting memories. Make sure to join the festive skate nights, live music performances, and themed celebrations throughout the season.

Harbor Walk of Lights

Key West’s Harbor Walk of Lights offers a spectacular nautical-themed light display honoring the maritime history of the Key West waterfront. Expect to see the 20-foot Fishing Buoy Tree, a 16-foot Nautical Christmas Tree, and the iconic Key West Lobster Trap Tree glittering with holiday lights. The waterfront transforms into a dreamscape of colorful lights and nautical displays featuring everything from animated sea turtles to dancing dolphins under brightly lit holiday palm trees. Stroll along three blocks of sparkling holiday lights and displays around the Key West Bight Marina and Historic Seaport, making it an unmissable festivity among Key West events.

Key West Holiday Parade

The Key West Holiday Parade brings holiday spirit parading down Duval Street with floats by civic leaders, churches, and community groups. Kicking off at Truman and White Streets, winding through Old Town, and concluding at Caroline Street, the event culminates with Santa and Mrs. Claus. This is a must-see traditional Key West celebration that typically includes around 50 entries. Spectators can watch the parade up close from the judges’ stand at the corner of Duval and Fleming streets.

Schooner’s Wharf Bar Lighted Boat Parade

Before settling down for holiday feasts, Key West locals and boat owners create stunning holiday-themed light displays for the Lighted Boat Parade. The event at the Schooner Wharf Bar features a procession of brilliantly lit boats that sail through the Key West Bight. Thousands of viewers and an esteemed panel of judges enjoy the parade, which can be best appreciated aboard the fully-stocked Fury Catamaran.

New Year’s Eve Red Shoe Drop

One of Key West’s glamorous drag queens descends from the top of the New Orleans House in a big red pump at the stroke of midnight, attracting tens of thousands of spectators every year. The Red Shoe Drop is not just one of the best New Year’s Eve parties in the country, but it’s also inclusive, fun, and uniquely Key West. Families, friends, and revelers of all ages come together to witness this spectacular event, often covered by national media.

New Year’s Eve Lowering of the Pirate Wench

Celebrate the New Year with a nautical twist at the Key West Bight, where Evalena Worthington, co-owner of the Schooner Wharf Bar, is lowered from the towering mast of the tall ship America 2.0. Amidst pirate-costumed crew members, the evening features live music, holiday drink specials, and complimentary festive hats and noisemakers. Enjoy the cannon fire and jubilant horn blasts as the pirate wench descends and the new year begins.

Sloppy Joe’s Conch Shell Drop

For thirty years, Sloppy Joe’s has celebrated New Year’s Eve with the traditional Conch Shell Drop. What started with a manually lowered conch shell now draws crowds who gather at the corner of Duval and Greene Streets for a synchronized countdown. Experience the lively atmosphere both inside and outside the bar, all while enjoying the unforgettable drop of Key West’s favorite conch shell.

Key West Things to Do this Holiday Season

See the Nutcracker Key West

Forget snow-covered landscapes, Nutcracker Key West offers a whimsical Christmas tale with an island twist. Sugarplum fairies mingle with sea fans and mice soldiers in a Key West setting. This unique performance infuses the classic holiday ballet with local flair, making it a perfect holiday adventure for the entire family. Since its inception by Joyce Stahl, this reimagined ballet has become a beloved part of Key West’s cultural landscape.

Book a Private Holiday Party Charter

For a luxury holiday experience, consider booking a Private Holiday Party Charter. With groups of up to 14, this two-hour cruise offers an elegant holiday setting aboard the seas of Key West. Savor a champagne-inspired gourmet cheese buffet, free-flowing Chandon Champagne, and an outstanding wine list, beers, and holiday food. It’s a fabulous way to celebrate the season surrounded by the tranquil waters of Key West.

Take a Holiday Tour with Old Town Trolley Tours

Hop aboard Old Town Trolley’s Holiday Sights & Festive Nights Tour to enjoy a sparkling panorama of decorated historic Key West homes. The tour showcases the best of the island’s festive decorations and provides an entertaining commentary on Key West’s holiday traditions. It’s one of the top things to do in Key West this season for those wanting to kick back, relax, and soak in the holiday spirit island-style.

Stay with Bayfront Suites

When planning your holiday itinerary in Key West Florida, staying at Bayfront Suites allows easy access to all the festive Key West things to do. Conveniently located, we offer luxurious rentals that serve as your perfect home base. Whether you’re here for the holidays or just to escape the winter chill, our Key West luxury rentals provide an unrivaled experience of comfort and elegance. When attending Christmas events in Key West, be sure to book our best holiday rentals in Key West for festive, memorable experiences. Don’t miss out on these exciting things to do in Key West to make the most of your holiday season. Book with us, Bayfront Suites, for the ultimate holiday experience!