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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 Lights and Sights 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 Lights & Sights 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


December 12-17, December 20-23 and December 26, 2021.
6:30pm & 8:00pm.


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!



2021 Holiday Events

December 4, 11, 18, 19.
Santa at the Shops at Mallory Square
291 Front Street, Upstairs
Visit with Santa at the Shops at Mallory Square to add some magic to your holiday season. Visits with Santa begin on Saturday, December 4. Kids of all ages can visit Santa in the North Pole located upstairs in the historic Shops at Mallory Square to share their holiday wishes and pictures with the man in red. You decide your Santa Magic and can sit with Santa or have a socially distanced experience. For the younger set, letter writing stations and a mail box will be on hand.

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