beautiful white hammock at the pool area of property

Holly Jolly Key West Holidays

Every November and December in Key West, holiday magic lights up the air as we prepare America’s southernmost city for a visit from the North Pole’s most famous resident and his eight tiny reindeer. Though it would be impossible to list all the fantastic holiday happenings in store, here are a few of our favorites: 

Key West Harbor Walk of Lights at the Historic Seaport
Wed 11/23 – New Year’s Eve

Journey to the edge of the bight to enjoy a dazzling display of holiday decorations, including the famous Key West Lobster Trap Tree, the 16’ Nautical Christmas Tree, the 20’ Fishing Buoy Tree, and a stunning variety of light sculptures on nautical themes.

Key West Hometown Holiday Parade
Sat 12/3, 7pm

When the locals decide to put on a parade, you know it’s going to be a fantastic affair. Claim your spot along the route to witness elves, sugar plum fairies, reindeer (or craftily disguised horses—we’re not sure which), and lots of festive floats make their way from Bayview Park up Truman Avenue and Duval Street. 

The Holiday Lighted Boat Parade of Stock Island
Fri 12/9, 5:30pm 

If you miss the Hometown Holiday Parade, not to worry, you still have a chance to catch Stock Island’s own Holiday Lighted Boat Parade. Co-hosted by the Perry Hotel & Marina and the Rotary Club of Key West, this event promises a spectacular array of live entertainment, boats outfitted with radiant tropical holiday décor, and a chance to take photos with the Jolly Old Elf himself. Join the fun as a spectator, or enter your boat to win one of several cash prizes.

Schooner Wharf Annual Key West Lighted Boat Parade
Sat 12/10, 8pm

The day after the Holiday Lighted Boat Parade of Stock Island, stick around for the Schooner Wharf Annual Key West Lighted Boat Parade, featuring vessels of all sizes decked out with Christmas tree masts, antlered sea horses, skipper Grinches, Santas in scuba gear, and many more imaginatively maritime takes on traditional holiday themes and characters.

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