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night time picture of trolley in front of Boston skyline and holiday lights
nighttime picture of a trellis with Christmas lights in Boston
Nighttime picture of Faneuil Hall in Boston during Christmas with various trees decorated in holiday lights

Seasons Greetings!

From its colonial beginnings and puritanical past, Boston has become the favorite place for many to celebrate the Holidays each year, and there is no better way to experience the season than aboard an Old Town Trolley Holiday Sights & Festive Nights Tour!

Visiting Boston is great at any time of the year, but this year, winter just got even better. You’ll be able to take in the fun and merriment of the holiday season from your front row seat as our festive storytellers share tales of past, present and future celebrations.

The Holiday Sights & Festive Nights Trolley Tour is the perfect way to experience the magic of the season, riding through town as carolers fill the night air with music, and each tour finishes with a gourmet marshmallow filled hot chocolate bomb and a decadent Holiday treat.

Old Town Trolley’s Holiday Sights & Festive Nights Tour: A Great Way to Celebrate the Holiday Season!

Tour Highlights

San Diego Christmas Lights Tour by Old Town Trolley
Entertaining festive characters on each trolley.
Festive Tour Guides
Nighttime Boston picture of holiday decorations including holly leaves and pinecones and a full moon and Faneuil Hall in the background
Learn about the history of the Holidays in Boston.
Seasonal Stories
hot chocolate bomb
Finish your experience with a complimentary gourmet marshmallow filled hot chocolate bomb and a decadent Holiday treat.
Complimentary Treats
glass container wrapped in a ribbon and holding candy canes; in the background are holiday lights
All guests will receive festive gifts and a unique souvenir of the Boston Holiday Tour.
Festive Gifts
nighttime picture of a trellis with Christmas lights in Boston
Make this your new annual tradition with friends and family!
Boston Holiday tour
Designed especially for the New England winters, our festive trolleys will give you more than just a warm welcome.
Heated Trolleys

Tickets & Schedule


Trolley Stop 1:
The Marriott Long Wharf, 200 Atlantic Ave.


2023 dates coming soon. Please check back.
Check reservations calendar for departure times.


Approximately 90 minutes.
Reservations are required.

Transportation will be provided at 5:40pm from Trolley Stop #12 (Welcome Center) to the Marriott Long Wharf to start your tour upon request. Return transportation to Stop #12 will be provided after the last tour of the evening.

*Tour dates are subject to availability.

price tag


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2023 Holiday Events

Coming soon.

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