Welcome to Holiday Season in Paradise
December in Key West means warm breezes instead of snow boots. Whether you are here for a long weekend or the whole month this guide will help you plan every festive stop.
Signature Holiday Events
December 5 - Holiday Village and BeLighted Bike Ride
On Friday December 5, 2025 Wesley House Family Services hosts its Holiday Village with games rides food trucks and the magical BeLighted Bike Ride down Duval Street! It is family friendly with photos with Santa and even “snow” in paradise. Check schedule and registration at the Wesley House site.
December 6 - Key West Hometown Holiday Parade
The city then kicks off the season with the Hometown Holiday Parade on Saturday December 6, 2025 starting around 7 pm. Expect floats marching bands and plenty of candy along Truman Avenue and Duval Street. Bring a chair stake out a spot early and wave to Santa as he rolls by. More details are on the city and tourism sites.
December 12 - Holiday Concert and Bazaar at the Custom House
The Key West Art and Historical Society transforms the Custom House into a festive concert and artisan bazaar in mid December. Shop local art listen to choirs and enjoy a big island style light show all in one evening. Event information and exact times are listed on the KWAHS events page.
Festival of Trees and Historic Inn Tours
Throughout December beautifully decorated trees fill the Custom House and local historic inns open their doors for ticketed tours with seasonal bites and live music. It is one of the best ways to step inside classic Key West homes all dressed up for the holidays.
Waterfront Lights and Boat Parades
Harbor Walk of Lights and Bight Before Christmas
Starting in late November and glowing through the new year the Harbor Walk of Lights at the Historic Seaport delivers more than sixty thousand lights along the waterfront including a fishing buoy tree nautical Christmas tree and lobster trap tree. Stroll from Greene Street to the Ferry Terminal for photos snacks and live music.
December 13 - The 34th Annual Schooner Wharf Lighted Boat Parade
On Saturday December 13 2025 the famous lighted boat parade fills the Bight with sailboats catamarans and yachts wrapped in lights. Music starts around 6pm in the evening and the parade kicks off at 8pm with viewing all along the Harbor Walk and at Schooner Wharf Bar. Many local charters including Fury and Sebago offer special parade viewing sails so you can watch from the water.
Fury Sunset Sail with Santa
Early in the month Fury Water Adventures hosts a special sunset sail with Santa that benefits Wesley House. Kids ten and under sail free adults donate to the charity and everyone enjoys snacks drinks and Key West views with Santa on board. Click Here
Active Adventures and Races
December 13 - Rudolph Red Nose Run
A Positive Step hosts the Rudolph Red Nose Run five kilometer race mid month starting at Southernmost Beach Cafe. Wear holiday pajamas or costumes and join locals for a fun run by the water. Additional charity walks and runs often pop up so check local calendars as your trip approaches.
December 14 - Key West Triathlon
On Sunday December 14 2025 athletes swim bike and run along the Atlantic waters and Higgs Beach during the annual Key West Triathlon with both sprint and Olympic distances. It is a great spectator event and a fun way to earn that extra slice of holiday key lime pie.
Tours Lights and Family Fun
Holiday Lights Trolley and Train Tours
Old Town Trolley and the Conch Tour Train both offer Holiday Lights tours from early to late December. Hop aboard for about an hour and cruise past the most decked out neighborhoods with special holiday glasses cookies and cider. These tours sell out so booking ahead is smart.
Holiday Sights and Festive Nights
Some Old Town Trolley departures are branded as Holiday Sights and Festive Nights featuring expert guides stories about local traditions and the best light displays on the island. It is a great first night outing if you just arrived in town.
Ghosts and Gravestones
If you like a little spooky with your sparkle the Ghosts and Gravestones tour operates year round and is extra atmospheric on cooler December evenings. Learn about haunted mansions restless spirits and shipwreck stories while rolling through Old Town after dark. Click Here
Harbor Walk Winter Wonderland and Waterfront Winter Wonderland
In addition to the Harbor Walk of Lights the Coffee Butler Amphitheater at Truman Waterfront transforms into Waterfront Winter Wonderland with an ice rink rides games live music and visits with Santa throughout much of December. It is perfect for kids and anyone who wants a taste of winter without the snow. Click Here
Key West Cooking Show
For food lovers the Key West Cooking Show offers “dinnertainment” where chefs prepare island inspired meals in front of you while sharing stories and local history. It is a fun evening indoors when you need a break from the beach. Click here to schedule
New Years Eve in Key West
Key West is famous for its unforgettable New Years Eve “drops” and 2025 will be no exception. The island fills with music lively street parties and huge crowds from Duval Street to the waterfront. Instead of a traditional disco ball Key West rings in the new year with a collection of one of a kind countdowns that you will not find anywhere else.
The Conch Shell Drop at Sloppy Joes
The most iconic celebration happens at Sloppy Joes Bar where a giant illuminated conch shell is lowered from the roof at the corner of Duval and Green Street. It is broadcast live every year and draws a massive crowd.
Fun fact:
New Years Eve 2025 marks the thirty second year of the Conch Shell Drop. The very first shell in 1993 was lowered by hand using a simple frame. A brighter and more elaborate version debuted in 2005 and has been the star of the show ever since.
The Red High Heel Shoe Drop at Bourbon Street Pub
Just a few blocks away Bourbon Street Pub hosts one of the most photographed events in the Keys the Red High Heel Shoe Drop. A glamorous drag queen descends inside a giant red high heel shoe as the crowd counts down to midnight.
This celebration is fun bold and very Key West. Performances begin around nine in the evening and VIP balcony tickets at the New Orleans House usually go on sale in December. They sell out quickly so booking early is a smart move.
Celebrate with Live Music on Sunset Pier at Ocean Key Resort
Ocean Key Resort offers a vibrant waterfront New Years Eve featuring live music cocktails and dancing on Sunset Pier. At midnight a giant Key lime wedge drops into an oversized margarita glass creating one of the most tropical countdowns you will ever see.
Good to know:
This is a private ticketed party with limited availability. Tickets normally sell out early.
Travel Back in Time at the Great Gatsby Party at First Flight
First Flight Island Restaurant and Brewery hosts a glamorous Great Gatsby themed celebration every year. Guests dress in 1920s inspired outfits enjoy gourmet food stations an open bar and music from a live DJ.
As midnight approaches excitement builds for the venue’s own themed drop often inspired by First Flight’s aviation history such as a “plane drop.”
Good to know:
This is a popular ticketed event that often sells out weeks in advance.
Ring in the New Year at Schooner Wharf Bar
Schooner Wharf Bar celebrates with a maritime themed party called Rigging in the New Year. Live music drinks and food carry the festivities throughout the day until the dramatic Lowering of the Pirate Wench from the mast of the tall ship America 2.0.
A glowing countdown clock lights up the harbor and a cannon blast marks the moment the new year arrives. Most people begin gathering around 9pm though the live entertainment starts earlier in the day.
Explore Duval Street and Mallory Square
If you prefer a night of bar hopping and spontaneous fun Duval Street is the place to be. Thousands gather for the various drops and parties happening throughout the night and Mallory Square hosts its festive Sunset Celebration with performers and vendors leading into the evening.
Expect big crowds lively music and a nonstop celebration up and down Duval Street.
A Tropical Countdown Like No Other
From pirate wenches and giant margarita glasses to conch shells and high heels there is no shortage of creativity on New Years Eve in Key West. Many restaurants bars and charter companies also offer special dinners sunset sails champagne toasts and waterfront fireworks.
Because these events fill up fast booking early is the best way to secure your perfect island countdown experience.
Explore KeyWestTed's Team Digital Brochure
We welcome you to take a few minutes to flip through our interactive team brochure. It walks you through who we are how we market properties our track record and case studies from around the island.
You can view the brochure online here - Click to view
Your Key West Realtor All Year Long
Whether you are planning a December getaway or already call the island home, my team is here for ALL your real estate needs.
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Key West Ted
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