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Old Town Trolley Old Town Trolley Tours Key West sightseeing tours
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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.

Along with the awesome sights and excellent narration highlighting fun facts about the island, you’ll also enjoy some complimentary tasty treats like cookies and hot cider. 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!

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
Cheer with cider and cookies!
Holiday Spirit

Tour Schedule


Mallory Square




60 minutes

price tag

Adults: $19.95*
Children (4-12): $10.50*
Ages 3 and under ride free. Must ride on parent’s lap.
*5% city fee added to all tickets.


icon in the shape of two tickets

December 6, 12, 13, 14, 16: 5:45pm, 6:00pm, 6:15pm.

December 18, 19, 21, 22, 23: 5:45pm, 6:00pm, 6:15pm, 7:00pm, 7:15pm, 7:30pm

Tickets must be purchased online.

VIP passes cannot be accepted or used for Holiday Tours. Reservation based tickets are non-refundable. You may reschedule up to 24 hours in advance of tour time.

Large group bookings are not guaranteed to sit together.

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!



2019 Holiday Events

When you come to the Conch Republic for the Holiday Lights & Sights Tour, make sure you stick around because the island is swimming with tons of holiday events to explore!

Second & Fourth Sunday in December
The Sheriff’s Animal Farm
1:00pm – 3:00pm
5525 College Road, Key West, FL


December 14, 2019
Annual Gingerbread House Making Event
11:00am – 3:00pm
Oldest House & Gardens Key West, 322 Duval St.
Free Event


December 14, 2019
Fury Water Adventures – Lighted Boat Parade
The Key West Lighted Boat Parade is an annual affair that combines with the Harbor Walk of Lights to celebrate the Christmas Holiday. Each year a variety of boats decorate their sails, masts and hulls with Christmas Lights and festive cheer. This year Fury Water Adventures will be in the parade! They’ll be serving up fresh appetizers, drinks and live music for a night that is guaranteed to get you in the holiday spirit!


December 15, 2019
Conch Republic Seafood Company’s Annual Holiday Classic Car Show
11:00am – 3:00pm
Greene & Elizabeth Streets
Please bring an unwrapped toy for Monroe County Domestic Abuse Shelter. VOTE for the “Peoples Choice” award. Awards for: BEST engine, interior, original & custom, Best in Show. See classic cars from every era decked out for the holidays! Non-member cars may enter same day FREE with an unwrapped toy!


December 22, 23, 27 and 28
A Very Truman VIP Experience – Little White House Holiday Tours
6:30pm – 8:30pm
Imagine how it must’ve been to celebrate the holidays with the Trumans in the 1940s. An impeccably appointed tree decked with the finest ceramic and glass ornaments. The intoxicating aroma of cinnamon and spruce. Now you can travel back to a simpler time with this exclusive tour with some very special treats in store!


December 25, 2019
Fury Water Adventures Christmas Ultimate Adventure
Trip features sailing on a state-of-the-art catamaran, snorkeling North America’s only living coral reef, parasailing and jet skiing.


December 31, 2019
Fury Water Adventures New Year’s Eve Sunset Cruises
This is one of those Key West New Years Eve Events you just don’t want to miss. You can choose from a variety of different energy levels on your trip. Some of the options include the Commotion on the Ocean, which is the rocking Live Music Sunset Sail or a romantic Champagne Sunset Sail, for you and your special someone.


December 31, 2019
Key West New Year’s Eve Celebrations
Rooftop Conch Shell Drop – at Sloppy Joe’s, 305-296-2388. Drag Queen Drop in a giant Red High Heel – at Bourbon St. Pub, 305-293-9800. Pirate Wench down the Schooner mast – at Schooner Wharf Bar, 305-292-3302. Key Lime Wedge drop into giant Margarita – at the Ocean Key Resort.

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