Whether you’re just breezing through or enjoying an extended stay, we’ve got several options to choose from to help you maximize your time in Boston and still see the best first!
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Our Boston tour is 13 miles long and two hours from start to finish, but our route is designed for you to hop off at any stop, explore a Boston attraction or neighborhood, and hop back on when you are ready to resume your Boston sightseeing experience.
The tour visits South End, Back Bay, Historic North End, Beacon Hill, the Theater District, Downtown Crossing, the Seaport District, and Charlestown.
For more information, go to tour schedules.
We operate the city’s largest fleet of sightseeing vehicles and this allows us to pick up and drop off more frequently than any other tour company. The frequency of the trolleys depends on the time of the year, traffic, and weather conditions, but typically it is every 20 minutes. April – October: Daily. 9am – 5pm. November – March: Daily. 9am – 4pm.
The Freedom Trail is a 2.5-mile urban brick walking path that takes in different historical Boston sites. The trolley tour gets you close to many of the sites along the Freedom Trail, as well as all the other major points of interest around the city of Boston. Our Boston tours help you explore the entire Freedom Trail without having to walk it all on foot.
If you’ve ever visited or plan to visit Boston, you’ll know that getting around can be a bit tricky. However, there’s an easy solution to that — the Old Town Trolley. Hop on, and you’ll be able to explore some of the city’s best attractions without the bother of driving or navigating traffic. Exploring Boston without a car is easier than you think thanks to Old Town Trolley. From historic sites and shopping to amazing food and beautiful beaches, Boston has something for everyone, and the trolley takes you to all the best spots.
Boston’s most picturesque neighborhood is Beacon Hill, an area that boasts stunning architecture, cobblestone streets, and charming boutiques. For those who want to make the most of their time and see Beacon Hill from a unique perspective, hopping on the Old Town Trolley is the way to go.
The first stop of the Old Town Trolley in Beacon Hill is at the Massachusetts State House. From this towering location, visitors can take in the stunning panoramic views of the city and the Charles River. The tour guide will provide visitors with fascinating facts about the State House’s history, including the famous codfish atop its dome, the symbol of Boston’s fishing industry.
The trolley then takes visitors through the heart of Beacon Hill’s residential area, a place filled with old brick houses, antique gas lamps, and postcard-perfect scenery. The highlight of this tour is undoubtedly the stop at the Old North Church, known as the church that started the U.S. Revolution.
Continuing down Beacon Hill, the trolley stops at the legendary Cheers bar, also known as the set of the hit TV show, “Cheers.” Visitors can sit at the same bar where Norman and Cliff once did, take photos, and enjoy the historic décor.
Boston’s Beacon Hill is a hidden treasure of American history, and the Old Town Trolley is the perfect way to experience it. From the State House’s panoramic views to the blue skies to stopping at a bar where everyone knows your name, this tour offers visitors a unique way to see the city’s hidden treasures while learning about Boston’s vibrant past.
Here are some of the must-see attractions that you can explore on the Old Town Trolley Tour:
1. The Freedom Trail: This iconic 2.5-mile-long trail takes you through 16 significant historical sites that were crucial to the American Revolution. You’ll see the Massachusetts State House, Paul Revere’s House, Old North Church, the USS Constitution Museum, and more. The Freedom Trail is a fascinating way to learn about the city’s rich history.
2. Acorn Street: Located in Beacon Hill, this street is a throwback to Colonial times with its cobblestone streets, gas lamps, and impeccably preserved 19th-century homes. Its houses are some of the oldest in Boston, and their exteriors have remained mostly unchanged for over a century. Acorn Street’s timeless look and feel, mixed with its New England charm, has made it a favorite among filmmakers.
3. Harvard University: Located in the nearby town of Cambridge, Harvard University is one of the world’s most renowned institutions of higher learning. You can tour the campus and visit the Harvard Museum of Natural History.
4. Quincy Market: This colorful marketplace is a shopper’s paradise, with more than 100 vendors selling everything from souvenirs to food. You can indulge in some classic Boston dishes such as clam chowder or a lobster roll.
5. Bunker Hill Monument: This 221-foot granite obelisk commemorates the Battle of Bunker Hill, which was a pivotal moment in the American Revolution. You can climb to the top for a stunning view of the city.
Boston transforms into a picturesque and vibrant city at night, and it offers plenty of things to do for those who are up for some nighttime fun. If you’re visiting Boston this summer, there’s no better way to explore the city after dusk than taking the Boston Summer Night Tour by Old Town Trolley. You’ll be able to visit historic landmarks and hidden gems that are illuminated by the city’s glow. From the Old North Church and the USS Constitution, Boston has a plethora of iconic and historic landmarks to explore. From the stunning harbor views to the twinkling skyline at night, explore these sites under the cover of darkness, where the ambiance and atmosphere are simply magical.