Key West Christmas 2021 | Key West Events

Enjoy Christmas in Key West

Key West is a special place to enjoy the Christmas season. During the holidays, Key West lights up with fun festivities and offers a unique atmosphere to celebrate this exciting time of year. If you’re looking to escape the cold, and enjoy a Christmas holiday full of sun and artistic events, Key West is the perfect place.

Over the past 20+ years, we’ve created hundreds of Christmas Vacations in Key West. We love sharing this special time of year with our guests. On this page, we highlight some of Key West's best Christmas events.

Key West Christmas

The Key West 2021 Christmas Schedule is Yet to Be Determine


Check out last year's schedule:

Key West Lighted Boat Parade 

The Lighted Boat Parade is a classic Key West holiday event. Staring at 8 pm on December 15th, tons of well-lit water vessels float onto the Key West Bight and Harbor. Every boat picks a theme and is judged on creativity and splendor.

This Key West holiday event brings the whole island together. It’s always fun to see all the creative light shows shining on the water. Key West goes all out for this fun event. The captains’ meeting is on December 13th at 8 pm on the upper deck of the Schooner Wharf. For detailed information, Contact Schooner Wharf Bar at (305) 292-3302. 

December 15 , at 8 pm

Old Town Trolley's Holiday Light and Sights Tour

Presented by Old Town Trolley, the Holly Jolly Holiday tour is a great way to enjoy the lights of Key West. Leaving from Mallory Square, this 60-minute tour takes you all over the island and gives you a special glimpse of Key West’s special holiday spirit.

December 8-9: 6 pm, 7 pm, 8 pm
December 15-16 and December 19-23:
6 pm, 6:15 pm, 6:30 pm, 7:15 pm, 7:30 pm, 7:45 pm

Nutcracker Key West

Nutcracker Key West mixes the classic Nutcracker production with Key West’s tropical environment and rich cultural history. Produced bi-annually at the Tennessee Williams Theater, Nutcracker Key West is a phenomenal performance that highlights the spirit of Key West. In 2018, Nutcracker Key West will feature a brand-new set.

December 8-15 at 7:30pm
Matinees: Dec 8,9,15,16 at 2:30pm Tennessee Williams Theatre

Eaton Street Stroll

Five venues with five different shows! Stroll down Eaton Street between St Paul's Church, The Studios of Key West, Key West Theatre, Old Stone Church and Tropic Cinema to enjoy 4 concerts and a movie for a wonderful Christmas mood setter.

December 9th 4:00 PM, Gather at St Paul's Church for opening events 

Key West Holiday Classic Car Show

Check out the main parking lot on Caroline and Margaret Street for a cool car show that supports a good cause. The Southernmost Car Club offers a free car show that and collects unwrapped toys for the Domestic Abuse Shelter. Classic cars from every era will be decked out for the holidays.

December 17th 

Thanks for your interest in Key West during the Holidays. This is truly a wonderful time of year to visit our special island. We hope to see you on Key West for Christmas.

Stay with Us for Christmas