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picture of key west old town trolley at night driving past a house decorated with holiday lights
Key West homes decorated with Christmas Lights
Key West house with purple and white Holiday lights

Old Town Trolley's Holiday Sights & Festive Nights Tour

Seasons Greetings!

No need to gas-up the snowblower this year if you’re planning a holiday escape to the Conch Republic! Here, ‘Christmas chill’ means rockin’ your flops and kicking back island-style and one of the best ways to do that is hopping a ride on Old Town Trolley’s Holiday Sights & Festive Nights Tour! The Southernmost City is all a twinkle, as the locals decorate their historic Key West homes in a splendid cascade of lights and other decorative touches to see who can outdo the other in a friendly, holiday-inspired competition – see all the best decorations on our holiday tour.

Take in awesome sights and excellent narration highlighting fun facts about the island. Give you and yours the gift of Key West this year!

Tour Highlights

Just a quick look-see at all the cool stuff you’ll be enjoying on your holiday tour!

Key west houses during the holidays
The best way to Experience the holidays in Key West
Holiday Cheer
key west house lights
Get fun facts about Key West
Great Narrators
key west holiday lights tour
Make this your new annual tradition with friends and family!

Tickets & Schedule


Mallory Square


2023: December 8-23.
6:30pm, 7:00pm, 8:00pm and 8:30pm.


60 minutes

price tag


icon in the shape of two tickets


Key west houses during the holidays

Key West Holiday Lights Contest

Tis the season for some friendly, holiday-inspired competition to see which Key West home can out bling all the others during the Annual Key West Holiday Lights Contest.

This contest for bragging rights and a $500 First Place prize really brings out the creativity and love of the community of area homeowners as they work their decorative skills decking their homes with all manner of light displays that turn this sunny paradise into a winter wonderland!



2023 Holiday Events

November 22
Lighting of the 2023 Harbor Walk of Lights
Harbor Walk Plaza at Greene and Elizabeth St.
5 pm

November 25
Holiday Artisan Market
Studios of Key West, 533 Eaton Street

December 1
Pet Pictures with Santa
Key West Harbor Walk
6 pm – 8 pm

December 2
Key West Holiday Parade
7 pm
Parade begins on Truman at White and heads to Duval Street ending at Eaton Street.

December 8
Key West Art & Historical Society Annual Holiday Concert and Bazaar
281 Front Street
5 – 9 pm

December 9
Schooner Wharf Annual Lighted Boat Parade
Key West Harbor Walk
8 pm

December 10
Christmas at the Sheriff’s Animal Farm
5525 College Road
1 pm – 3 pm

December 15-30
Key West Waterfront Winter Wonderland
Coffee Butler Amphitheater at the Truman Waterfront Park

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