Ensconce yourself within the ocean-inspired design of our rooms while looking out over the harbor and pools from your private balcony.
Seas‑on’s Greetings from paradise! From Thanksgiving week through New Year’s Eve, Key West and the Historic Seaport light up with holiday traditions, parades by land and sea, family‑friendly markets, and three iconic New Year’s Eve countdowns—all within an easy walk of The Marker Key West Harbor Resort. Use this guide to explore the can’t‑miss holiday events, festive markets, tours, and merry moments that make the season in Key West truly unforgettable.
Photo credit: Island Living: Florida Keys.
Holiday Lighting Ceremony & Kickoff at Key West’s Official Christmas Fun Headquarters
Thursday, November 14 | 5:30 pm to 7:30 pm | The Parlour at the Avalon Guest House
Kick off the season at Key West’s Official Christmas Fun Headquarters at The Parlour inside the Avalon Guest House, part of our sister property at Southernmost Beach Resort.
This year’s theme, “Nothing is Sweeter than Key West at Christmas,” sets the stage for a season full of island cheer and festive fun. There will be Christmas karaoke, candy cane shot specials, ugly sweater nights, trivia, ornaments, and more festive fun.
The Official Key West Christmas Fun Headquarters will be open daily from 3 pm to 7 p.m. beginning November 15 and continuing throughout the holiday season.
Lighting of the Bight: Harbor Walk of Lights Kickoff
Wednesday, November 26 | 5 pm to 8 pm | Historic Seaport
The “Bight Before Christmas” Lighting of the Bight officially launches the 2025 holiday season at the Historic Seaport.
At 5 pm, live music fills the air at the Greene and Elizabeth Street plaza as Santa and Mrs. Claus begin greeting families and passing out treats. The Fishing Buoy Tree lights up at 6 pm, followed by the Lobster Trap Tree lighting at 7 pm at Margaret Street Plaza in the Old Lands End Village—complete with cookies and candy canes for the kids.
Three blocks of sparkling lights and nautical displays illuminate the Seaport nightly through New Year’s Eve, honoring Key West’s maritime history. The Harbor Walk of Lights begins just outside
The Marker’s front gate—a festive, photo-worthy stroll you can enjoy every night of your stay.
Photo by Carol Tedesco / Florida Keys News Bureau
Learn More: Bight Before Christmas
5th Annual BeLighted Bike Ride & Holiday Village
Friday, December 5 | Holiday Village 5 pm to 9 pm | Bike Ride Begins at 8 pm | Coffee Butler Amphitheater
Another favorite and one of Key West’s most creative holiday traditions begins at the Coffee Butler Amphitheater. Expect colorful, quirky, and festive bikes, along with a spirit of island magic for all ages. The event benefits Wesley House Family Services, supporting local children and families in need.
The family-friendly Holiday Village is the pre-party to the ride and features more than 20 community booths with games and activities, carnival rides, bounce houses, local food trucks, and live performances. Kids can enjoy photos with Santa, sweet treats, and more. All of that is taking place between 5 and 9 pm.
At 8 pm, the main event begins with a glowing procession of bikes departing from the Amphitheater and parading along Whitehead and Duval Streets in a dazzling display of holiday spirit. Whether you decorate your own bike or cheer from the sidelines, it is one of the brightest and most joyful nights of the season.
Photo by Ginger Monteleone | Wesley House Family Services
Learn more: Holiday Village & BeLighted Bike Ride 2025
Key West Holiday Parade
Saturday, December 6 | 7 pm | Truman Avenue to Duval Street
It’s the one night a year when the whole island turns into a holiday block party. The Key West Holiday Parade is where locals, schools, bands, and families come together, not just to watch, but to be part of the show. Everyone joins in as floats decked out in creative holiday flair roll down Truman Avenue toward Duval Street, candy flying, crowds cheering, and Santa closing out the night.
The parade kicks off at 7 pm at Truman Avenue and White Street, beside Bayview Park, and makes its way down Duval Street. Grab a spot along the route and get ready for a parade that will create merry memories you'll cherish forever!
Custom House Holiday Concert & Bazaar
Friday, December 12 | 5 to 8 pm | Custom House Museum
A Night of History, Art, and Holiday Magic (Free)
Experience one of the most enchanting nights of the season at the Custom House Holiday Concert & Bazaar, hosted by the Key West Art & Historical Society.
The 1891 Custom House transforms into a glowing outdoor market featuring handmade art, jewelry, and island-inspired gifts. Enjoy live holiday music from choirs and steel drum bands as a dazzling animated light show illuminates the museum’s historic façade.
It’s the perfect pre-dinner stop for a festive evening in Old Town.
Photo courtesy Key West Art & Historical Society
Learn more: Holiday Concert & Bazaar
The 34th Annual Schooner Wharf Bar/Absolut Vodka Lighted Boat Parade
Saturday, December 13 | Festivities begin at 6 pm | Parade at 8 pm | Historic Seaport
The 34th Annual Schooner Wharf Bar Lighted Boat Parade transforms the harbor into a sparkling seascape of lights. Boats of all shapes and sizes sail by, decked out with creative holiday designs and nautical cheer.
Enjoy the festivities from Schooner Wharf or along the Harbor Walk—just steps from The Marker, for some of the best boat parade views.
Photo by Carol Tedesco / Florida Keys News Bureau
Learn more: Lighted Boat Parade
Merry Market at Southernmost Beach Resort
Saturday, December 13 | 4 to 8 pm | Southernmost Beach Resort
Celebrate the season seaside at the Merry Market at our sister property, Southernmost Beach Resort, a festive showcase of local artists, food, live music, and holiday cheer. Meet Santa, sip tropical cocktails, and shop for unique handmade gifts while enjoying a family-friendly evening by the ocean.
Learn more: Merry Market at Southernmost Beach Resort
Key West Artisan Market
Sundays, December 14, 21 & 28 | 10 am to 2 pm | Higgs Beach
Spend your Sunday morning strolling the Key West Artisan Market at Higgs Beach. Each market features local art, fresh food, music, and island-made treasures. It’s one of the best ways to shop local and experience Key West’s creative side during the holidays.
See full schedule: Key West Artisan Market
6th Annual Holiday Cookie Throwdown at The Marker
Wednesday, December 24 | 12 pm | Poolside at The Marker Key West Harbor Resort
It’s back and sweeter than ever! The 6th Annual Holiday Cookie Throwdown invites hotel guests and locals to bring their best cookie creations for a holiday taste test and friendly (and delicious) cookie competition. Taste, vote, and celebrate the season, one cookie at a time.
Learn more: The Marker Key West Resort Calendar
New Year’s Eve: Pirate Wench Drop at the Seaport
Wednesday, December 31 | Midnight | Schooner Wharf Bar
Ring in the new year at the Lowering of the Pirate Wench, one of Key West’s most iconic celebrations. At midnight, Schooner Wharf’s pirate wench, Evelena Worthington, descends from the mast of a tall ship while oohs, ahhs and cheers fill the air along the Seaport.
The best part? It’s steps away from The Marker.
Other New Year’s Eve Countdowns Within Walking Distance
Photo by Rob O’Neal / Florida Keys News Bureau
Your Key West Holiday Questions, Answered
Q: What are the top holiday events in Key West in 2025?
A: From the Lighting of the Bight to the Schooner Wharf Lighted Boat Parade and The Marker’s own Cookie Throwdown, Key West is full of festive events throughout the season.
Q: Where can I see the best Christmas lights in Key West?
A: The Harbor Walk of Lights at the Historic Seaport is a must-see, featuring nautical displays and trees decorated with buoys and lobster traps.
Q: Is The Marker Key West close to the main holiday events?
A: Yes! The Marker sits just steps from the Historic Seaport, where many of Key West’s most iconic holiday events and light displays take place.
The holidays in Key West sparkle with lights, laughter, and island traditions, and The Marker puts you right at the heart of it all. When Key West gets nauti and nice, there’s no better place to unwrap the magic of the season. #lovethemarker
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Waterfront Luxury
Ensconce yourself within the ocean-inspired design of our rooms while looking out over the harbor and pools from your private balcony.
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