Christmas in Key West


Christmas in Key West - Old Town Manor


It’s the most wonderful time of the year! From lighted bikes to boats decorated top to bottom, there’s no shortage of holiday cheer in the Conch Republic. Here’s our guide to spending the holidays in Key West.


Pet Pictures with Santa

Get your pets’ picture taken with Santa Clause at the foot of William Street on the Harbor Walk of Lights. The event is free with lots of giveaways. Proceeds benefit the Boys and Girls Club of the Keys.


Christmas in Key West - Santa in hammock

Photo by Cayobo, courtesy of Flickr


Key West Annual Hometown Holiday Parade

One of the earliest events in the holiday line up and a local favorite is the Annual Holiday Parade. This festive parade features local children of all ages, marching bands, floats, and a special appearance by the man in red! The route includes Truman Avenue, White Street, and Duval Street.


Key West Lighted Bike Parade

Light up your Key West cruiser bicycle and let the parade begin! And don’t forget your registration fee: One unwrapped toy to be donated to the Key West Holiday Shop where struggling families can choose toys for their children to open on Christmas. The parade starts at Bayview Park, and rides through the streets of Old Town Key West. Get more info and register in advance here.


Christmas in Key West - lighted trolley tour

Photo by dcwriterdawn, courtesy of Flickr


Conch Train Holiday Lights Tour The famous Conch Train and the Conch Trolley change their routes this holiday season to showcase the holiday lights and decor throughout residential neighborhoods on the island. The tour lasts an hour and begins with festive cider and cookies. See the Old Town Manor concierge or click here for tickets. Holiday Lights Tours run most days of the holiday season.


Key West Holiday Historic Inn Tour Two Fridays in December, tour around a handful of Old Town Key West’s most beautifully decorated inns and B&Bs while sampling holiday treats and beverages. The locals don’t skimp on the holiday décor around here! If you love holiday decorations, this tour is perfect for you. Trolleys provide transportation, but you’re welcome to ride bikes at your own pace.


Parade of Paws

The Parade of Paws benefiting the Florida Keys SPCA is one of our cat and dog loving staff’s favorites! Participants collect donations from their friends and family before taking their dogs down to the Higgs Beach dog park to show off their four-legged friends. Afterwards stick around for the Holiday Bazaar including food vendors, entertainment, and dog pictures with Santa! Check in is at 9am. 


Christmas in Key West - lighted boat parade

Photo by Marcus, courtesy of Flickr


Lighted Boat Parade

It wouldn’t be Christmas in Key West without the Schooner Wharf Lighted Boat Parade! Key West locals compete for the best in show by decorating their vessels from top to bottom and showing off their creations in the Historic Seaport. From rowboats to tall ships, you’ve never seen a boat parade like this. Winners take home cash prizes and bragging rights. Watch from shore at all the bars and restaurants along the Harbor Walk or ask our concierge how to get on a lighted boat yourself!


Holiday Classic Car Show

Join the Conch Republic Seafood Company in welcoming classic cars from every era decked out for the holidays. Vote for the people’s choice award, and check out the unique shopping boutiques in the area for last minute gifts. Unwrapped toys will be collected for the Monroe County Domestic Abuse Shelter. Free to attend.


Key West Dachshund Walk

On New Years Eve at noon, a few hundred dachshunds and their owners will stroll through the Old Town neighborhood on Fleming Street between Whitehead and Duval Streets. This is a must-see for dog lovers!


Christmas in Key West - Southernmost Point

Photo by @marco, courtesy of Flickr


Ready to celebrate the season in Key West? Check our holiday availability here!