Tropical Spirits! The Magic of Key West Holiday Fest

As one of America’s top tropical holiday destinations, Key West is a small town that’s big on holiday cheer. Nothing embraces its holiday spirit more than Key West Holiday Fest.

This annual month-long celebration which spreads good cheer all over our small island, kicks off on Wednesday, November 27 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 and stretches along the Key West Historic Seaport and Key West Bight Marina.

The entire harbor area, including a Fishing Buoy Tree, fresh pine Nautical Christmas Tree and the original Key West Lobster Trap Tree, shimmer and shine with hundreds of thousands of festive holiday lights. This year, the island-wide celebration also includes a special tribute to the late Jimmy Buffet.

Things really kick into high gear starting on Saturday, November 30 when The Studios of Key West stages its annual Holiday Market from 9 am – 2 pm. The weekend culminates with a fun Tree Trimming Party & Toy Drive at Schooner Wharf Bar which starts at 6 pm.

On Friday, December 6, Wesley House launches it’s annual Holiday Village & Belighted Bike Ride at Truman Waterfront Park from 5 – 9 pm. On Saturday, December 7, Key West’s very own Hometown Holiday Parade rolls out more holiday cheer starting at 7 pm from the intersection of Truman Avenue and White Street. On Sunday, December 8, it’s time for the Eaton Street Christmas Stroll which begins at 3:30 pm at St Paul’s Episcopal Church. The 8th Annual Holiday Concert & Bazaar draws a fun crowd on Friday, December 13 and takes place from 5 – 9 pm at Key West’s Custom House Museum. Also not-to-be-missed: Key West’s famous Schooner Wharf Lighted Boat Parade which shoves off on Saturday, December 14 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 Home Tours on Friday, December 6 and again on Friday, December 13; the Annual Key West Holiday Home Tours on December 27 – 28; 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 New York City’s annual Times Square Ball Drop. Topping it all off is a plethora of live concerts, art openings, and theatrical performances including a sensational production of Nutcracker Key West. This island interpretation of the fabled holiday ballet opens on Thursday, December 5, and plays for two festive weekends: Friday, December 6 – Sunday, December 8; and then again on Friday, December 13 – Sunday, December 15.

If a balmy tropical get-away adorned with twinkling lights and fun festivities popping up all over the island is your idea of a fun way to spend the holidays, then Key West is your place in the sun!