Boston Hop-On Hop-Off Trolley Tour with 11 Stops

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.

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.

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.

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.

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.

The tour visits South End, Back Bay, Historic North End, Beacon Hill, the Theater District, Downtown Crossing, the Seaport District, and Charlestown.

You may start your Old Town Trolley Tour at any of our convenient stops. Click on Map and Stops to see a list of our stops with information about the attractions and points of interest at each stop.

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.

This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

The minimum age to participate is 4. This tour requires at least one adult to accompany children..

If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.

If you find a date and time that works for you, book it NOW because things always sell out at this time of year.

Accessibility information for the Boston Hop-On Hop-Off Trolley Tour with 11 Stops is as follows:

Detailed check-in instructions – including meeting point address, Google map, and parking information – for Boston Hop-On Hop-Off Trolley Tour with 11 Stops will be included in your confirmation email from City Sky Diving. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.

Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.

If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.