As one of America’s top tropical holiday destinations, Key West is a small town that’s big on holiday magic. And nothing embraces its holiday spirit more than Key West Holiday Fest.
This annual month-long celebration kicks off on Wednesday, November 26 at 5 pm with the highly anticipated “Lighting of the Bight.”
Every night, starting on Thanksgiving Eve, Key West’s Historic Harbor Walk hits the switch for a breathtaking display of holiday lights. This spectacular “Harbor Walk of Lights” stays lit nightly through New Year’s Eve, stretching along the Key West Historic Seaport and Key West Bight Marina. The dazzling display also includes a 6-foot fresh pine Nautical Christmas Tree, an original 20-foot Key West Lobster Trap Tree, and a special tribute to Jimmy Buffett. Holiday music starts at 5 pm with the lighting at 6 pm.
Things really kick into high gear starting on Saturday, November 29, when The Studios of Key West throws open the doors for its annual Holiday Artisan Market. With over 20 artisans showcasing locally produced items, it’s the perfect place to pick up a unique, handcrafted gift. Takes place from 10 am – 2 pm.
But that’s just the tip of the iceberg.
On Friday, December 5, Wesley House launches its annual Holiday Village & Belighted Bike Ride. The magical Holiday Village is home to lots of fun rides, games, crafts, food vendors, local performances, Santa photo ops, and more. Takes place from 5 – 9 pm at Truman Waterfront Park.
On Saturday, December 6, Key West’s very own Hometown Holiday Parade rolls out more holiday cheer, starting at 7 pm from the intersection of Truman Ave and White St. For a great view, head on over to the Oldest House Museum at 322 Duval St for a festive Holiday Porch Party that kicks off at 6 pm.
On Sunday, December 7, Schooner Wharf Bar in Key West’s Historic Seaport hosts its annual Tree Trimming Party & Toy Drive. The event includes Santa’s Southernmost Schooner Workshop, where local artists and authors sign and sell original works for holiday gift-giving.
The 9th Annual Holiday Concert & Bazaar draws a fun crowd on Friday, December 12, and takes place from 5 – 9 pm at Key West’s Custom House Museum. The celebration boasts some of the island’s finest artisans, musicians, and choirs; lots of great food and holiday libations, as well as a holiday light show projected on the face of the Custom House.
Also not-to-be-missed: Key West’s famous Schooner Wharf Lighted Boat Parade, which shoves off on Saturday, December 13 at 8 pm from the Historic Seaport.
During the entire month of December, there will be lots of other merry events, as well, including the oh-so festive Key West Historic Inn Tours (Date TBD); the Annual Key West Holiday Home Tours on December 26 – 27; holiday island lights tours via the Conch Tour Train and Old Town Trolley; seasonal artisan markets and bazaars; and multiple New Year’s Eve “Drops” that spoof NYC’s annual Times Square Ball Drop.
Topping it all off is a plethora of live concerts, art openings, and theatrical performances that will be happening throughout the season.
For more information and late-breaking details, hit up keywestholidayfest.com
Happy Holidays!
Photos: Courtesy Carol Tedesco







December is such a glorious time in Key West, and I’ll be basking in all those joys starting tomorrow. Thank you for the list of “must-dos” during my stay.