The Mermaid & The Alligator at 729 Truman Ave. is one of the enchanting locations that will be visited and explored by revelers during the Friday, December 17, 2021 Holiday Historic Inn Tour. As one of America’s top tropical holiday destinations, Key West is a small town that’s big on holiday cheer. And 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, kicked off on Wednesday, November 23, with the Lighting of the Bight: Key West Harbor Walk of Lights. Every night, starting on Thanksgiving Eve, Key West’s historic Harbor Walk hits the switch for a breathtaking display of holiday lights. The harbor area includes a Fishing Buoy Tree, fresh pine Nautical Christmas Tree, and the original Key West Lobster Trap Tree, which shimmer and shine with hundreds of thousands of festive holiday lights. This “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.

Island City House, located at 411 William Street in Key West, is one of the enchanting locations that will be visited and explored by revelers during the 2021 Holiday Historic Inn Tours, taking place on December 10 and 17. (Photo: Carol Tedesco/Key West Holiday Fest)Throughout the season, you can indulge in all kinds of festive holiday happenings, including the Eaton Street Holiday Stroll kicks off December 4 at 5 pm from The 
Studios of Key West, followed by a fun Tree-Trimming & Toys for Tots Party at Schooner Wharf Bar at 6 pm. The Annual Parade of Paws is on December 10 from 10 am – 2 pm at Higgs Beach. The Schooner Wharf Lighted Boat Parade on December 10. Key West’s Holiday Historic Inn Tours on December 9 and 16. Holiday Makers Markets at The Studios of Key West on December 18 from 9 am – 2 pm. Key West Home Tours on December 28 and 29 from 2 – 4 pm. 
 Throughout the month, there will be a merry range of other events, as well, 
including a Hometown Holiday Parade, festive island lights tours via the Conch Tour Train, Old Town Trolley, seasonal artisan markets, bazaars, and multiple New Year’s Eve “drops” that spoof New York City’s annual Times Square Ball Drop.

Holiday Fest Deck The HallsTopping it all off is a plethora of live concerts, art openings, theatrical performances, and so much more.

If a balmy tropical get-away adorned with twinkling lights, historic inns decked out in their holiday finest. If fun festivities popping up all over the island is your idea of a fun way to spend the holidays, Key West is your place in the sun!

For more information on individual events, see pages 31-38.
Late-breaking updates and details at keywestholidayfest.com

Happy holidays!