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Boston History Beyond the Freedom Trail

Boston, United States

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Experience hosted by Bob

2 hours
Includes food
Up to 9 people
Hosted in English

What you'll do

We begin on the historic Long Wharf, the focus of Boston Harbor. First, we’ll head past the Rose Kennedy Greenway, State Street, and the historic Custom House Tower. Then, I'll lead you toward the famous Faneuil Hall and Quincy Market, which both boast stunning views. Moving into the heart of Downtown, we'll stop in front of the Old State House and site of the Boston Massacre. Was it really a massacre or maybe just great propaganda for the Revolution? It's up to you to decide!

A short trek through Downtown Crossing past the Old City Hall will take us to one of the most historic places in the country, King’s Chapel, the first Anglican church in New England. Whenever possible, I'll take you inside - if we’re lucky, we might just get to hear its pipe organ being played.

On most weekdays (government hours only!) you have a chance to see the government at work inside the inspiring, historic, and beautiful Massachusetts State House. Outside, take in the views of modern Boston, including the skyscrapers of Downtown and the tallest building in New England: the John Hancock Tower.

We continue our journey through Beacon Hill, where you’ll have a chance to take in the quintessential architecture of Boston’s red brick row houses. Finally, we arrive at the beautiful Boston Public Garden, one of Boston’s favorite green spaces.
Other things to note
Please wear casual clothes appropriate for the weather, and comfortable walking shoes. This tour is mainly outside.
We begin on the historic Long Wharf, the focus of Boston Harbor. First, we’ll head past the Rose Kennedy Greenway, State Street, and the historic Custom House Tower. Then, I'll lead you toward the famous Faneuil Hall and Quincy Market, which both boast stunning views. Moving into the heart of Downtown, we'll stop in front of the Old State House and site of the Boston Massacre. Was it really a massacre or maybe just great propaganda for the Revolu…

Bob'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.
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What's included

  • Food
    A surprise local treat!
From $32
/ person
Fri, Nov 27
1:00 PM - 3:00 PM
$40 per person
$40 per person
Sat, Nov 28
1:00 PM - 3:00 PM
Join 2 other guests
$40 per person
$40 per person
Sun, Nov 29
1:00 PM - 3:00 PM
$40 per person
$40 per person

Meet your host, Bob

Host on Airbnb since 2019
  • 34 Reviews
  • Identity verified
I have a deep love and appreciation for the history, diversity, and unique culture of Boston. Sharing my love for Beantown with visitors (first-timers and frequent visitors alike) is a passion of mine. Boston's big draw is obviously American history, but there's so much more to it than what you learned in school! I've spent time discovering the lesser-known stories on and off the Freedom Trail, learning about the historic architecture in Beacon Hill, and getting to know a barkeep or two, so that I can connect you to the Boston of old and new. Of course there's the postcard historical sights, but I'll also take you behind-the-scenes and inside of some of the locales overlooked by many Boston visitors (and even locals!). On my tours, you'll receive personal attention from a real, Boston local and a unique experience that you won't forget!
I have a deep love and appreciation for the history, diversity, and unique culture of Boston. Sharing my love for Beantown with visitors (first-timers and frequent visitors alike) is a passion of mine. Boston's big draw is obviously American history, but there's so much more to it than what you learned in school! I've spent time discovering the lesser-known stories on and off the Freedom Trail, learning about the historic architecture in Beacon Hill, and getting to know a barkeep or two, so that…
Co-hosts:
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Where you'll be

Go beyond the Freedom Trail and experience modern Boston through the city’s incredible history. From the iconic Boston Harbor, into the heart of beautiful Beacon Hill, by King’s Chapel, through Boston Public Garden and Downtown, and (weekdays only) into the Mass. State House! Join me on an experience that promises to connect you to the Boston of old and new - including a drink at my favorite neighborhood watering hole!

Rated 5.0 out of 5 from 34 reviews.

Adrian
February 2020
First time used Airbnb for tour and thought it was well organised and Tim, our guide, was an encyclopedia on dates in Boston's history. He was enthusiastic about the history and made the tour interesting and interactive. It gave us an opportunity to see inside buildings we may not have gone into and see what history they had. Great fun for the afternoon.
First time used Airbnb for tour and thought it was well organised and Tim, our guide, was an encyclopedia on dates in Boston's history. He was enthusiastic about the history and ma…
Jennine
January 2020
My freedom trail tour guide was with Conner and he was amazing. Very friendly and welcoming. Awesome at telling each locations historic background, very informative and fun. We also visited a pub for a drink which was very nice.
Ramesh
January 2020
Great value for the price! A quick 2 -3 hour walk in Downtown Boston, through a few important historical buildings, stories about them and personalities associated with them. All with a super friendly guide, Connor.
Margaret A
January 2020
Connor was our a friendly and kind guide for this tour. He did a wonderful job sharing interesting stories about our early American history in Boston. Especially the amazing points on what was the real meaning behind symbols and declarations of speech. As well, he provided factual information on many of the historical figures involved with the American Revolution. Despite the cold and rainy day, we enjoyed this tour with Connor.
Connor was our a friendly and kind guide for this tour. He did a wonderful job sharing interesting stories about our early American history in Boston. Especially the amazing points…
Laura
January 2020
We absolutely love the tour. Bob provided a unique experience, we would’ve never gone to any of the locations we experienced by ourselves. Bob is knowledgeable and entertaining. Thank you for a great experience.
Maria
December 2019
Bob was wonderful at explaining everything. And his sense of humor really made the tour fun and interesting. My family and I enjoyed this experience. Bob was super friendly, inviting and was a great resource for dining recommendations.

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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 9 guests of all ages can attend.