About Boston Strolls

So long, and thanks for all the great memories!

Starting in 2014, Boston Strolls will not be offering regularly scheduled public tours.

Our guides continue to be awesome, and they have gone on to start a podcast. Subscribe to HUB History to hear hosts Nikki and Jake share their favorite stories from Boston's rich history.

Watch the "Travel and Tours" and "History" sections of the Cambridge Center for Adult Education catalog for their occasional courses. And follow @HUBhistory on Twitter for a daily dose of Boston history and trivia.

Frequently Asked Questions

Boston is a walking city, and a city with much historical significance. Basic Freedom Trail tours will tell you everything you already know about Boston, with all the dates and details that would make your high school history teacher proud. But – the secret is – the Freedom Trail is easy to self-guide! The red brick path and the abundance of historical plaques and markers give you the flexibility to explore at your leisure.

At Boston Strolls our goal is to show you something new, to add value to your experience in our city by introducing you to people, places, and stories that you will not find on any other tour. We travel off the beaten path, literally, to give you a glimpse into Boston’s past that goes beneath the surface and beyond the ordinary. We will leave you with some tales and anecdotes that you won’t soon forget!

We limit our Beacon Hill and North End tours to 20 people to ensure that each guest can hear and see the guide, and so that the group can move easily from place to place. With the broad sidewalks in the Back Bay, we can accommodate up to 25 at a time.
Reservations are required for your convenience. Without a reservation we cannot guarantee that there will be space for you on the tour. Also, if there are no reservations for a particular day we may not send out a guide.

The Beacon Hill Uncensored tour will discuss the neighborhood’s history of vice, including adult themes such as murder and prostitution. We consider the content of the tour to be PG-13, and are happy to answer more detailed questions over the phone.

Our other tours are suitable for all ages.

Private tours are an excellent option for your club, party, convention, reunion, or occasion. We will provide you with your own tour guide at a time that fits your schedule. Private guides are available for any of our advertised tours, and we will be happy to work with you to tailor content to fit your theme or interests. Please call 617-383-9255 to discuss your options.
Tours will depart on time as long as weather conditions are safe. In case of lightning or other severe weather, a tour may be cancelled, delayed, or rescheduled. Boston Strolls will contact you in the event that severe weather prevents an on time departure.
Reservations that are cancelled by phone or email with 24 hour notice will be fully refunded or rescheduled. (For a 10:30am Saturday tour, reservations must be cancelled by 10:30am Friday) Reservations that are cancelled within 24 hours will be refunded or rescheduled with a $5 fee. A refund or rescheduling is not available if you do not cancel by phone or email prior to departure.
Tours are available year round, but our peak season is April to November. Outside those months, please email to confirm availability rather than booking online.
Our tours do not include any stairs, but there are challenges such as steep hills, brick sidewalks, and rough cobblestone streets. Please email us if you have specific needs or concerns.
Our gas lamp logo and the printed rack card were designed by Amy Kucharik. The website is powered by Bootstrap and the Worthy theme.


Available as private group tours only, contact your guide.


We were so enthralled

This was GREAT! My husband and I wanted to do something other than wander through stores. I suggested a walking tour, he did the research, and I made the reservations. What a GREAT day! Jake was our tour guide and was so knowledgeable and passionate about the history of Boston. We were lucky, we went in Dec. on a cold snowy day, so were were the only two people on the tour. Although it was cold (my chin went numb), we were hardly bothered by it. We were so enthralled with the history of how Back Bay was created. We will ABSOLUTELY go on another tour- I’m hoping for the Bad Medicine tour, but I’m sure the Beacon Hill tour will be just as exciting!

Sara on Yelp

I give the experience an A+

I used a Groupon for two adults on the 10:30 Saturday a.m. tour 11/24. Nikki Stewart is smart, funny, and extremely knowledgeable. Besides the environment being beautiful and the history interesting, what showed through was Nikki’s passion for her subject and her ability to convey that information to her audience. I give the experience an A+.

Amy via email

Knowledgeable and personable

My girlfriend and I were in town from Arizona and wanted to take a tour that would give us some background on the city of Boston. The Back Bay tour was fantastic. The guide was very knowledgeable and personable. The environment was really laid back and we were able to ask questions and move at our pace. The level of knowledge of the tour guide was impressive, I would recommend this tour for anyone looking to gain a better understanding of how the back bay came to be.

Grant on TripAdvisor

I recommend it without hesitation

My friend and I had a very enjoyable time. Our guide was articulate, humorous and his passion for the development and history of back bay was contagious. My friend and I have lived in Boston for many years and we learned many new and interesting facts. I recommend it without hesitation for both Bostonians and visitors.

Sarah via email

We’ve never been on a walking tour before and I think this one spoiled us

My husband bought a Groupon for this tour the day before while we were on vacay in Boston barely skimming the description but thought it would be a good thing to do for us while we were visiting. We’ve never been on a walking tour before and I think this one spoiled us - it’s exactly the type of unusual and interesting facts that we like to know! Our tour guide, Nikki, was very knowledgeable and had a charismatic way of telling historic stories which included murder, scheming, naked quakers, the Boston strangler and beheading. She also took us to picturesque spots with cobblestone roads and pointed out some historically famous houses.

N.P. on Yelp

A born storyteller

We took the 1:00 Uncensored Beacon Hill Stroll on Saturday and had a delightful time despite the chilly wind. The guide, Nikki, was not only extremely knowledgeable, but a born story teller. We will definitely spread the word and be back for another stroll ourselves.

Alan & Katherine via email

Fun facts that will make you smile

Lovely and interesting walk thru Beacon Hill. This tour brings you to places where the little know facts about this area come to life. An easy 90 minutes walk with a knowledgable guide. Learn some fun facts that will make you smile.

Bestfive on TripAdvisor


Groupon: 91% Positive

Hundreds of Happy Guests!