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Insider's Boston Walking Tours

Rated 5.0 out of 5 from 10 reviews.Boston, United States

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Experience hosted by Bill

3 hours
Includes drinks
Up to 4 people
Hosted in English

What you'll do

Your safety comes first. There will only be one family per tour, and we will observe social distancing. Everyone is expected to wear masks. If that is a problem for you, please don't book tour.

We explore every aspect of the city as we walk through 5 different neighborhoods. Guests learn about Boston’s past and recent history, our unique culture and attitudes, the food and restaurant scene and more. Each 3-hour tour is personalized, and with no more than 6 people, there is plenty of opportunity to explore the specific topics. I provide a personal, authentic understanding of the city and its people on this private walking tour of one of America's most historic cities.

Among the unique sites we visit and topics we discuss are as we walk are:
The beautiful reading room and art galleries in the Boston Public Library
19th century dioramas that illustrate the history of the Back Bay
Frederick Law Olmsted's Emerald Necklace, a 7 mile connected series of parks
The statue that commemorates the first use of ether in surgery
The gruesome murder of George Parkman, a prominent Bostonian, in the 1800's
The history of race relations in Boston, from the abolitionist movement to today's
tarnished reputation
Site of the first organized football game in the US
The story of the development of the MBTA, America's first subway
A hidden shopping courtyard
Your safety comes first. There will only be one family per tour, and we will observe social distancing. Everyone is expected to wear masks. If that is a problem for you, please don't book tour.

We explore every aspect of the city as we walk through 5 different neighborhoods. Guests learn about Boston’s past and recent history, our unique culture and attitudes, the food and restaurant scene and more. Each 3-hour tour is personal…

Bill's commitment to safety

This host committed to Airbnb’s COVID-19-related safety and cleaning guidelines—including adhering to social distancing guidelines, practicing good hygiene, and ensuring that all participants wear a mask.
Learn more

What's included

  • Drinks
    Along the tour, we stop for a bathroom break and drinks.
From $125
/ person
Fri, Sep 25
10:00 AM - 1:00 PM
$125 per person
$125 per person
Sat, Sep 26
10:00 AM - 1:00 PM
$125 per person
$125 per person
Sun, Sep 27
10:00 AM - 1:00 PM
$125 per person
$125 per person

Meet your host, Bill

Host on Airbnb since 2014
  • 10 Reviews
  • Identity verified
I am an enthusiastic Bostonian and am passionate about the city, its history and culture and of course the people.

I am a 40-year Boston resident with a background in city planning
I am absurdly interested in Boston history and culture
I follow local issues such as the economy, crime, movies and transportation
I love to discuss Boston sports, including the Patriots. (But don’t hold that against me.)
I can talk about food and wine for hours and is always trying new restaurants
I am outgoing and love to meet new people
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Where you'll be

We visit 5 Boston neighborhoods - Back Bay, Beacon Hill, Downtown, North End and South End. We will see historic row houses, Copley Square's great architecture, the Public Garden and Commons, beautiful 19th century townhouses, Colonial Boston and the famous North Church. Along the way we will talk about how landfill created much of Boston, the first subway, Boston's famous citizens, fascinating Civil War history and modern Boston.

Rated 5.0 out of 5 from 10 reviews.

Erin
February 2020
This was a phenomenal tour. We left with a sense of Boston's history, the character of each neighborhood and a list of food/site recommendations to see the remainder of our trip. Bill personalizes the tour to what you're interested in - we told him we loved wine and he took us to a small wine store that had an incredible basement collection we got to look at. Bill knew the owners and they set us up with a few bottles to take home. It was a great tour - I would do it again when different visitors come into town. Thanks Bill!
This was a phenomenal tour. We left with a sense of Boston's history, the character of each neighborhood and a list of food/site recommendations to see the remainder of our trip. B…
Chris
January 2020
This was my second time visiting Boston and I was looking for an insider's guide to the city. Bill went above and beyond my expectations. On the tour Bill covered historic sites such as Boston Public Library, the Old North Church, and the Old State House along side newer sites such as the Boston Public Market (I highly recommend stopping here for lunch), the New England Holocaust Memorial (a very stirring memorial), and Rose Kennedy Greenway. I especially enjoyed the collection of maps in the library. I highly recommend taking Bill's tour it is worth your time and money.
This was my second time visiting Boston and I was looking for an insider's guide to the city. Bill went above and beyond my expectations. On the tour Bill covered historic site…
Genevieve
October 2019
I absolutely recommend this tour with Bill. Even if you have already done other tourist walks in Boston, Bill’s tour will give you the insider experience that will be unique to what he offers. In addition to visiting all of the historical sites of most interest and learning about them, you will gain an insider’s view of life in Boston and a true understanding of why this city is so special. Bill will also go out of his way to make sure and address all of your specific interests. Worth every dollar.
I absolutely recommend this tour with Bill. Even if you have already done other tourist walks in Boston, Bill’s tour will give you the insider experience that will be unique to wha…
Maria
October 2019
The tour with bill was very informative. I highly recommend this tour if you wan to get a better understanding of Boston’s history and culture. Bill was friendly and very professional. He pointed out a few restaurants to eat. It was an amazing experience!
The tour with bill was very informative. I highly recommend this tour if you wan to get a better understanding of Boston’s history and culture. Bill was friendly and very professio…
Laura
October 2019
Absolutely amazing. Bill was wonderful, was able to provide us questions to answers we didn’t even know to ask. Highly recommend, it was much better to be one on one instead of a group.
Michael
September 2019
Multi-topic tour of Boston, covering a lot of ground in a short time- very informative and useful for this historic city. Allowed us to more easily navigate and understand on a variety of levels.

Choose from available dates

30 available
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Things to know

Cancellation policy

Any experience can be canceled and fully refunded within 24 hours of purchase, or at least 7 days before the experience starts.

Guest requirements

Up to 4 guests ages 10 and up can attend. Parents may also bring children under 2 years of age.

More tips

Time and starting location can be changed to meet guest requirements

What to bring

Although the tour is not a hike, it does cover almost 4 miles. And brick sidewalks are charming but uneven. So you will need walking shoes and either a hat or an umbrella, as well as sunscreen. Let me know if you have any physical limitations

Please bring a mask for every participant. I will provide hand sanitizer if you don't have any.