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Boston tours
night time picture of trolley in front of Boston skyline and holiday lights
nighttime picture of a trellis with Christmas lights in Boston
Nighttime Boston picture of holiday decorations including holly leaves and pinecones and a full moon and Faneuil Hall in the background
Nighttime picture of Faneuil Hall in Boston during Christmas with various trees decorated in holiday lights

Seasons Greetings!

From its colonial beginnings and revolutionary past, Boston has since been one of America’s most essential and diverse cities in the USA. Visiting Boston is great any time of year; but this year, winter just got even better! For the first time, you’ll be able to take in the fun and merriment of the holiday season on an Old Town Trolley Holiday Lights and Sights Tour! You’ll have a front-row seat as you experience the dazzling lights and splendor of the season, riding through town as carolers fill the night air with music. Add complimentary seasonal beverages and snacks, and you’re all set for what promises to be a new holiday tradition in Beantown!

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

Tour Highlights

glass container wrapped in a ribbon and holding candy canes; in the background are holiday lights
Children will receive Santa hats and candy canes.
Surprises for the Kids
a red mug with hot cocoa and a gingerbread man cookie; and in the background are holiday lights
Seasonal beverages and snacks add to the magic of your evening.
Holiday Treats
San Diego Christmas Lights Tour by Old Town Trolley
Narrators in colonial attire or ugly sweaters will lead caroling to your favorite holiday music!
Holiday Cheer



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


December 1-30*, 2019. Closed December 25.
Time: From 6:30pm.


Approximately 90 minutes.
Reservations are required.

Transportation will be provided at 5:30pm from Stop 9, (Sheraton, Back Bay), and 5:50pm from Stop 13, (Trolley Stop Store, 3 Park Plaza), to The Marriott Long Wharf to start your tour. Return transportation at the end of your tour to these two locations will also be provided.

*Tour dates are subject to availability.

price tag

Retail: $26.25 • Online: $23.63

Kids 3-12:
Retail: $15.75 • Online: $14.18

2 & under: Free
Adults are asked to hold their infant child on their laps during the tour. Seats are for paid guests.

icon in the shape of two tickets

Reservations are required as space is limited for this popular tour.

GROUPS: For groups of 10 or more, please call for discounted group rates.

Reservation based tickets are non-refundable.

You may reschedule up to 24 hours in advance of tour time by calling (855) 396-7433.

2019 Holiday Events

Not only can you be a part of our very first Holiday Lights & Sights Tour, but you’ll be able to indulge in all Boston has to offer during this special time of year. Check out all the events around town!


Winter Season
Ice Skating at the Boston Common Frog Pond
Admission based on skater’s height. 58” and over: $6.00; under 58”: free. Skates and locker rentals not included. Voted Best Outdoor Skating Rink in the U.S. by USA Today.


November 29 – December 29, 2019
Boston Ballet: The Nutcracker
Prices vary; select showtimes
Whether you’re seeing it again or for the first time, The Nutcracker will capture your imagination and transport you to a magical world of brave toy soldiers and dancing snowflakes. Follow Clara as she embarks on her journey filled with colorful characters, breathtaking costumes, and majestic scenery. From the captivating dance of the Sugar Plum Fairy to the iconic snow scene, this classical set to the beloved music of Tchaikovsky continues to enthrall audiences of all ages.


December 4-31, 2019
Holiday Pops Holiday Performance
Select days at the Boston Symphony Hall
Ticket price varies by seating area
A performance filled with holiday music favorites, the traditional Pops sing-along, and a visit from Santa Claus himself! Started in 1973 by Boston Pops Conductor Arthur Fiedler, these concerts take place in the magical atmosphere of world-famous Symphony Hall that is beautifully decorated to evoke all the magic and charm of the season.


December 20-29, 2019
Disney on Ice: Worlds of Enchantment
Agganis Arena; select showtimes
Tickets start at $10
Rev up for non-stop fun with four of your favorite Disney stories at Disney On Ice presents Worlds of Enchantment. Thrill to high-speed stunts as Lightning McQueen, Mater and the crew of Disney•Pixar’s Cars race across the ice! Dive into adventure with Ariel and The Little Mermaid’s undersea kingdom. The toys are back in town with heroic action when Buzz Lightyear, Woody, Jessie and the Toy Story gang escape from Sunnyside Daycare and race for home in their most daring adventure! Plus, enter the wintry world of Arendelle with sisters Anna and Elsa and pals Olaf and Kristoff from Disney’s Frozen as they learn that true love comes from within. From wheels to waves, icy wonderlands to infinity and beyond, your family’s favorite Disney moments come to life at Disney On Ice presents Worlds of Enchantment.


December 27-29, 2019 
Secrets and Illusions Magic Show
Huntington Avenue Theatre
Prices vary; select showtimes
Tickets range between $49 – $79
Set on the dark and deserted streets of Paris, you’ll enter the legendary Louvre Museum, where an enchanting musical muse escorts you through galleries, while Ivan uncovers life’s greatest mysteries deep inside the priceless works of art, one dazzling illusion at a time. Watch someone face their greatest fear. Witness a person track down love in the most unexpected place, and another discover how the Laws of Attraction helps them find their purpose in life - might it be you?
Boston Globe boasts ”Magic with a Message.” It’s a 90-minute spectacular show which displays Ivan’s signature style of thought-provoking vignettes, audience participation, and storytelling. Paired with his remarkable approach to illusion, it will ultimately inspire, encourage and motivate you to discover your purpose and your destiny.

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