Holiday Concert & Bazaar
This festive free party features some of Key West’s finest artisans, musicians and choirs, along with a spectacular holiday light show. 281 Front Street.
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Holiday Historic Inn Tours – Night 2
Explore four beautifully decorated locations and their unique architecture and [...]
Nutcracker Key West
Tennessee Williams Theatre 5901 College Rd, Key West, FL, United StatesSugarplum fairies trade tutus for sea fans, and the battle [...]
Key West Waterfront Winter Wonderland
The Coffee Butler Amphitheater at Truman Waterfront Park will welcome revelers of all ages to a holiday wonderland with beautiful lighting displays, an ice skating rink, rides, attractions, music and more. Closed Christmas Eve and Christmas Day.
Old Town Trolley Holiday Lights & Sights Tours
Multiple nightly tours begin at Mallory Square and convey caroling passengers through magically decorated streets and neighborhoods.
A Positive Step 5K Rudolph Red Nose Run
Don your festive holiday jammies and join in the 15th A Positive Step 5K Rudolph Red Nose Run, starting and ending at the Southernmost Beach Café, 1405 Duval Street. Runners and walkers of all ages and abilities are welcome to participate; registrants receive a free t-shirt.
Conch Tour Train Holiday Sights and Festive Nights Tours
Multiple nightly tours depart from Key West High School and convey caroling passengers through streets and neighborhoods to revel in the magically illuminated city of Key West.
Nutcracker Key West
Tennessee Williams Theatre 5901 College Rd, Key West, FL, United StatesSugarplum fairies trade tutus for sea fans, and the battle [...]
Schooner Wharf Annual Key West Lighted Boat Parade
A glittering parade of illuminated watercraft. Arrive at the Key West Bight Marina at the Historic Seaport early in order to stroll through the magical Key West Harbor Walk of Lights.
Key West Waterfront Winter Wonderland
The Coffee Butler Amphitheater at Truman Waterfront Park will welcome revelers of all ages to a holiday wonderland with beautiful lighting displays, an ice skating rink, rides, attractions, music and more. Closed Christmas Eve and Christmas Day.
Old Town Trolley Holiday Lights & Sights Tours
Multiple nightly tours begin at Mallory Square and convey caroling passengers through magically decorated streets and neighborhoods.
Christmas Cantata concert
Fifth Street Baptist Church 1311 Fifth Street, Key West, FL, United StatesThe choir will perform a selection of contemporary music and Christmas carols.