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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.

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!

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!

Tour Schedule


Mallory Square


December 4-23 and December 26-29, 2020
6:30pm & 7:15pm
No tours offered December 5, 2020*
*Subject to change


60 minutes

price tag

Adults: $23.10*
Children (3-12): $13.65*
Ages 2 and under ride free. Must ride on parent’s lap.
*5% city fee added to all tickets.


icon in the shape of two tickets

Limited capacity: 35 seats per trolley.

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!



2020 Holiday Events

December 6
Annual Tree Trimming and Toys For Tots Drive
Schooner Wharf Bar
202 William Street

December 9
Eaton Street Stroll
Gather at St. Paul’s Church for opening events, 401 Duval Street
Five venues with five different shows! Stroll down Eaton Street between St. Paul’s Church, The Studios of Key West, Key West Theatre, Old Stone Church and Tropic Cinema to enjoy four concerts and a movie for a wonderful Christmas mood setter.

December 12
Key West Lighted Boat Parade
The Lighted Boat Parade is a classic Key West holiday event. Tons of well-lit water vessels float onto the Key West Bight and Harbor. Every boat picks a theme and is judged on creativity and splendor. This Key West holiday event brings the whole island together. It’s always fun to see all the creative light shows shining on the water. Key West goes all out for this fun event. The captains’ meeting is on December 11th at 8 pm on the upper deck of the Schooner Wharf. For detailed information, Contact Schooner Wharf Bar at (305) 292-3302.

December 17
Key West Holiday Classic Car Show
Check out the main parking lot on Caroline and Margaret Street for a cool car show that supports a good cause. The Southernmost Car Club offers a free car show and collects unwrapped toys for the Domestic Abuse Shelter. Classic cars from every era will be decked out for the holidays.

December 31
Schooner Wharf New Year’s Eve Celebration
The Unique Schooner Wharf Bar’s Seaport Tradition – Lowering of the Pirate Wench at Midnight. Party starts early in the day with three local and national acts – Party Favors – Champagne & Fun

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