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Expert Led Private Boston City Orientation

Likely To Sell Out
Select Date and Travelers
(Price varies by group size)
2 travelers
What to Expect
Boston is a vibrant city full of energy and history. It can be intimidating to know where to go, what to do, and how to find anything that's not already listed in a guidebook. In this two-hour sit-down chat and informal tour you will meet a local insider who knows Boston inside and out, what makes it different and special, and how to feel like a local while you are here. Ideal for your day of arrival, or very beginning of your trip.

We begin by meeting you at your hotel or a coffee shop near where you are staying. Your insider will show up with maps, schedules of events, and tons of know-how about using local transport, where to eat, and fun places to visit. We'll spend about an hour together discussing your trip and answering any questions about what to do while you're here.

Next, we'll hit the streets for a basic, 1-hour introduction to your neighborhood. We point out some local attractions—big and small—and orient you to your surroundings. Depending on where you're staying and what interests you we wander farther afield and explore the city more widely.

The goal of this experience is to give you insight into the local culture and pace of life in Boston so that you'll feel a little more local while you're here. We will explain local customs (How do you buy produce in the local market? What's the correct word for that breakfast pastry glistening with sugar? What is the local drink of choice?) and share with you a bit of the area's history. During these two hours together you will have the unique opportunity to learn from your insider's expertise and love for their city.
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Important Information
Departure Point
Traveler pickup is offered
The guide will meet the traveler(s) at their place of accommodation, please send accommodation information to the supplier of this tour when booking.
  • Privately Guided Tour
  • Expert Guide
  • Hotel Pick-Up: relevant hotel info is necessary from traveler
  • Gratuities
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Additional Info
  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Hotel pickup included: traveler's accommodations information is required to confirm this tour
  • Please send supplier of tour the ages of all participants at time of booking
  • Near public transportation
  • Tour operates rain or shine
  • Travelers should have a moderate physical fitness level
  • This is a private tour/activity. Only your group will participate
Cancellation Policy
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
About the operator

This tour has not yet been reviewed, but you can read what other travelers have to say about this operator.

By: Context
14 reviews
Jackson, Mississippi
Great Tour
Great way to spend three hours with a wonderful tour guide learning much about this part of Boston. Put on your
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Calgary, Canada
Thanks Jessica
Jessica gave us a great tour of North Boston. She’s a local who knows her city and wants to tell you about it.
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Naples, Florida
Incredible tour of “Irish” Boston
Our daughter gave us a custom Context tour of Boston as a gift. Our guide was Mark Callis, an author and
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Western Springs, Illinois
Revere Your Historical Roots in Boston’s North End
Walk with Christian VanDerslice as he connects the geography, people and events influencing the rise of Boston and
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Waverly, Nebraska
Tour Boston's North End with a local resident
My family enjoyed touring Boston's North End with Jessica. She was able to share the history and current culture
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Colorado Springs, Colorado, United States
“Boston North End, Historical Portrait of a City”
I took the 3 hour tour with our docent Jessica dello Russo. She is from that area of Boston so is very familiar
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Freiburg im Breisgau, Germany
Boston North End, Historical Portrait of a City
Our docent, Dr. Alex Goldberg, easily managed to narrate and explain the truly complex moves of Boston's history
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Kingston, Canada
See Boston's North End through the eyes of a local
We took a tour of Boston's North End with Context guide Jessica on June 29th. While it's true that Context tours
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West Palm Beach, Florida
Enjoyable and Insightful Tour of Boston's North End
I am so glad that I read about Context Travel's walking tours in Arthur Frommer's syndicated newspaper travel
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Sudbury Ontario, Canada
Great tour
We spent the day on a guided tour of Boston. Very informative and well worth spending the day here. The tour guide
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Washington DC, District of Columbia
An excellent tour!
I highly recommend Context tours. We took one Context tour in Rome which was outstanding. I proceeded to break
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Toronto, Canada
Back alleys, tombstones, soaring bookcases, and much more......
Jessica from Context Tours guided us through the Irish famine, past Uncle Tom Cabin's publisher's digs, the scull
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Stonington, CT
Beacon Hill Walk
We took the tour which was led by Jessica Dello Russo. Jessica is a Boston native with a degree in architecture
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Hopkinton, Ma
One of the best tours in Boston
We spent a perfect day in Boston with our wonderful guide,Jessica, from Context Boston. She is engaging, warm and
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Key Details
  • Context
  • Duration: 2h
  • Mobile Ticket Accepted
  • Instant confirmation
  • Languages Offered: English
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