Top Boston Historical Tours
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Leslie_M, Jun 2026
Entertaining way to learn about the city
Note: It is a lot of walking and Boston streets are often uneven pavement. Not necessarily the best option for folks with mobility or stability issues. That being said, we loved it! We try to do a walking history tour in most cities we visit and this provided a great background into the history behind the history you learn in school. Another warning, it was a rather large group, probably 30 people. But we had no issues hearing and it didn't slow us down. Do this on your first day and it'll give you an idea of places you may want to revisit later in your trip.
Lori_W, Jun 2026
Don’t miss this tour!
Sign up for this tour with Dan. I’ve been on several food tours and knew within 5 minutes this would be the best one ever. He’s remarkable, engaging, quick-witted, and so knowledgeable as a native Bostonian. He definitely has a gift for hospitality. He deserves all the praise because he makes this tour top notch.
On top of all of that the food was incredible and we were stuffed by the end.
If you take no other tour take this one.
Jeff_R, Jun 2026
Wicked Interesting
This tour was fun and very interesting. I’m from the Boston area and wanted to see what I was missing so I decided to see what visitors got to experience. I learned a lot about some of the big players in the American revolution. We probably walked about a mile total during the tour. Zoey was an awesome guide ! Very knowledgeable, friendly, passionate and friendly ! Highly recommended !
Michael_D, Jun 2026
Thank You Jesse
I wanted to thank City View Trolley Tours in Boston for accommodating my girlfriend and myself on our final evening in Boston. We were the last round and thankfully there was a driver named Jesse who was very courteous as we were his only 2 guests on his last trolley for the evening. It was a very busy time in Boston with traffic and right at rush hour and he did a very thorough job of narrating the tour and showing us everything that Boston had to offer, again.
I am not sure how he memorized all that information, but we learned quite a bit about Boston and got some nice photos and videos of the area. He even gave us suggestions on where to get dinner at Quincy Market. We are very thankful he was our trolley driver and made the whole experience a happy and memorable one.
Steve_P, Jun 2026
250 years!
This tour goes in depth of the history that took place with Paul Revere and the shots hurt around the world. You get to stand on the actual grounds where this happened and Coach our tour guide was amazing! His detail of what took place made you feel a part of it even though it was 250 years ago. The only thing I would say is I would’ve much rather had a little more time in the museums. But I know there’s only so much time in a day. Thanks for a great tour!
eula_a, Jun 2026
Review of Boston Underground Railroad-Black History
A great tour if you are interested in a better understanding of the role and relationships between Slaves, former slaves and white abolitionists in Boston and the rest of Massachusetts from the Revolutionary War through the Civil War.
We don’t talk about the this in the detail and specificity that Dave did on the tour. While we only went inside one building the visual aides and storytelling was most effective in giving a good picture of the past.
I really appreciate Dave explaining the statue of Colonel Shaw and the black troops he commanded at the end of the tour. The statue will forever have a more significant meaning to me.
Rebecca_S, May 2026
Fantabulous!
The Summer Nights was fantastic. Bailey was our guide and driver. He shared a lot of history throughout the different areas that we traveled through. He was very friendly and had a wonderful sense of humor. The crews on the charles river was amazing. The guides on our ride explained several of the buildings and the architecture around them. The sunset views were beautiful! Overall , I would highly recommend this experience to others.
Cathy_H, May 2026
An Afternoon of Deliciousness
I would highly recommend this tour! One suggestion: arrive hungry because there is a lot of amazing food along the way.
We started by sampling fresh-baked bread tucked away in an unmarked alley, and it was absolutely delicious. Next, we enjoyed traditional Italian pizza and fried rice balls at a historic family-operated eatery.
After walking off some of the food, we visited the Old North Church and learned fascinating history about Paul Revere. We then stopped for cannolis and coffee at a charming little café — both were fantastic.
From there, we passed the Paul Revere House and later enjoyed a balsamic vinegar tasting. While we sampled vinegars, our guide picked up sub sandwiches that we ate in a nearby green space.
By the end of the tour, we were completely full and very happy. It was a perfect combination of delicious food, local history, and a fun walking experience.
Shelby_C, Apr 2026
Lovely tour!
Our guide, Maddie, gave our group a wonderful tour of the North End and Freedom Trail! We hit up some delicious food spots that we will be talking about for a while. We particularly loved the Italian sandwich from Salumeria Italiana and the cappuccino and cannoli from caffe vittoria! Highly recommend for those looking to see Boston’s highlights in a short time.
Deborah_B, Apr 2026
Exceptional drivers/guides, very informative at stop 1
I used the City Trolley for two days,
The driver I had on my second day I think his name was Ervin was friendly, knowledgeable and informative. He was helpful as well to Spanish speaking riders
Loved meeting Willy by the stop 1 area, so very friendly and great recommendations for lunch
Arun_K, Apr 2026
Captain Pickles - one of the unsung heros of the American revelition
Captain Pickles (aka David) is a true patriot. His goal is to remind us of our American history and the important roles many individuals and groups played in the birth of this great nation. His depth of knowledge is exceptional, his sense of humor is wonderfu. We really enjoyed his tour. Thank you for your service David.
Adam_C, Nov 2025
Great way to introduce the city to you
The guide we had, Elizabeth, was so welcoming and informative. Great job of making the stories flow and tie into each other. It’s pretty crowded by other groups at every stop but she was easy to hear and understand the entire time. Great way to get a good introduction to the history and city streets.
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Boston and history go hand-in-hand, and there’s no better way to learn all about both than on Boston historical tours. While many focus on the 16-stop Freedom Trail, which traces the city’s history (particularly during the American Revolution), some add in other historic neighborhoods like the North End and Beacon Hill. You can choose to have a guide in period costume, and some tours also have food and drink components. There is even a narrated cruise along the harbor that recounts the waterfront city’s long history, as it passes the USS Constitution and the site of the Boston Tea Party.
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