Key West’s holiday season comes alive on the streets and on the water with markets by the beach, parades by land and sea, and the Official Christmas Fun Headquarters in the Southernmost City. Add lighted bikes and Santa sightings, and the lineup feels uniquely Key West. From Lighting of the Bight and the hometown Holiday Parade to the Schooner Wharf Lighted Boat Parade and New Year’s Eve on Duval Street, this guide shows what’s happening, where to watch, and when to be there.

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 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. Enjoy Christmas karaoke, candy cane shot specials, ugly sweater nights, trivia, ornaments, and more.

The Official Key West Christmas Fun Headquarters will be open daily from 3 pm to 7 pm beginning November 15th and continuing throughout the holiday season.

Avalon Guest House, 1317 Duval Street, Key West. 

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 as Santa and Mrs. Claus greet families and hand 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.

Three blocks of shimmering lights and nautical displays illuminate the Historic Seaport nightly through New Year’s Eve, honoring Key West’s maritime traditions.

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 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 Custom House Museum glows with holiday spirit during this annual event. Handmade art, jewelry, and island-inspired gifts fill the grounds, while choirs and steel drum bands perform beneath a brilliant animated light show on the 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 color and creativity. Boats of all shapes and sizes sail by, each decked out in dazzling lights and festive nautical designs. You’ll want to head down to the Seaport early to experience the glow as the harbor comes alive and the energy builds along the waterfront. The crowd gathers, the music starts, and captains proudly “deck the hulls” in true island style. For more than three decades, this beloved Key West tradition has celebrated the island’s maritime roots in festive fashion.

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

Let’s go holiday shopping seaside at the Merry Market at Southernmost Beach Resort. Browse local art and handmade gifts, meet Santa, sip cocktails, and enjoy live music with the ocean as your backdrop. We’ll be making spirits bright at our Merry Market, and we hope you’ll join us.

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. Featured 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 at our sister property, The Marker Key West Harbor Resort, invites guests and locals to show off their best cookie creations for a holiday taste test and friendly island competition. Taste, vote, and celebrate the season one cookie at a time.

Learn more: The Marker Key West Resort Calendar

New Year’s Eve: Big Red Shoe Drop on Duval Street

Wednesday, December 31 | Midnight | Bourbon St. Pub

Ring in the new year Key West style with one of the island’s most famous drops, the Big Red Shoe Drop on Duval Street. As midnight approaches, a glittering red high heel descends outside the Bourbon St. Pub Complex, only a few blocks from our Key West beach resort, while thousands of revelers fill the street to cheer, dance, and celebrate. Lights sparkle, confetti flies, and the crowd counts down to welcome the new year in true Key West fashion

In 2024, thousands of New Year’s Eve revelers watched Christopher Peterson drop in a Big Red Shoe outside the Bourbon St. Pub Complex to ring in the new year. So if you’re wondering what New Year’s Eve in Key West feels like, this photo says it all.

Photo credit: Carol Tedesco

Other New Year’s Eve Countdowns in Key West

Conch Shell Drop at Sloppy Joe’s: Another place to gather, and this time it’s in front of Sloppy Joe’s with the rooftop conch countdown at Duval and Greene.

Pirate Wench Descent from Tall Ship at Schooner Wharf: A pirate wench descending from the mast of a tall ship at Schooner Wharf Bar at the Seaport.

However you celebrate, there’s no better place to start the new year than right here in Key West.

May your holidays be merry, your memories bright, and your island days filled with warmth and wonder. #SoMoLife