Click for possible route/stop changes on the day of your tour here.
Skip to content
open search box Close
Manage booking

Season's Greetings

Discover the magic of wintertime in Key West and embark on a historical “Transportainment®” adventure!

Much in the same way Harry S. Truman retreated to his Little White House when things got a little too cool for comfort up in DC, Key West is where Santa comes to spread cheer and hang out in his Christmas-themed board shorts. This is one of the best places on Earth to celebrate the holiday season, just ask Conchy The Sandman and Rudy The Bottle-nosed Dolphin!

Be part of the fun on a Holiday Sights & Festive Nights Tour when the island goes all out with a glimmering festival of lights!

Your sleigh for the day will take you to some of the most resplendent island homes whose owners enter into a friendly competition for the most beautiful house on the block!

Old Town Trolley's Holiday
Sights & Festive Nights Tour


For a truly relaxing and festive Key West experience, head over to Mallory Square and board the Old Town Trolley. You’ll even be given special holiday lights glasses to ensure you enjoy all the sparkle. This 1-hour tour runs on select days throughout December.


holiday tour ticketsBUY TICKETS

Conch Tour Train Holiday Sights & Festive Nights Tour


Ho-Ho-Ho! Say goodbye to the snow and say hello to one of Key West’s most beloved attractions on a very special holiday evening! Once the holiday cheer has been stoked, it’s time to light up the night as we cruise through Key West and marvel at the shimmering dance of color emanating from the thousands of lights adorning the light posts, businesses, and homes of the Conch Republic. You’ll also get further into the spirit of things with some neighborhood caroling and a very special pair of glasses that enhances the light show to dazzling new levels.

key west holiday ticketsBUY TICKETS

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. Sponsored by Old Town Trolley Tours, Conch Tour Train, Historic Tours of America, and Key West Energy Services, this contest for bragging rights and a $500 First Place prize really brings out the creativity and love of 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!



Back to top