Boston Small-Group Food & History North End Freedom Trail Walking Tour 50 reviews
Boston, United States

  • Refundable
  • Printed Voucher/E-Voucher
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Keeping you safe during COVID-19
What you can expect during your visit
  • Face masks required for travelers in public areas
  • Face masks required for guides in public areas
  • Hand sanitizer available to travelers and staff
  • Regularly sanitized high-traffic areas
  • Transportation vehicles regularly sanitized
To know more, please refer additional information section of this tour
Activity Highlights
This is a typical itinerary for this product

Pass By: North End, Boston, MA 02109

Your North End to the Freedom Trail combines our North End Food Tour and our History and Highlights Tour to make up a brilliant half day tour that will give you a comprehensive introduction to our fair city.

We will begin at the lifeblood of Boston, the Boston Harbor with a walk through a scenic waterfront park. We’ll make our way to the heart of the North End, with views of some of the most historic sites. Tasty food is never far away in the North End. Your guide will introduce you to a small, hidden Italian bakery serving up fresh bread daily. A proper Italian salumeria is next, where you’ll have a chance to enjoy some Italian meats and cheeses. Next up, we’ll take in the energy of the North End’s busiest corridor, Hanover Street, where it’s time for a mid-tour break with your guide at a traditional Italian café.

Stop At: Old North Church & Historic Site, 193 Salem St, Boston, MA 02113-1123

You’ll hear stories about some of the most influential events that happened in Boston, including Paul Revere’s Midnight Ride. We will make our way to the Old North Church and step inside the hallowed walls.

Duration: 15 minutes

Pass By: Rose Kennedy Greenway, JFK Surface Road, Boston, MA 02111

A taste of pizza awaits at a neighborhood favorite and then we’ll cap off the North End food experience with samples of the best Italian pastries along the back streets of this delicious neighborhood.

Continue on with your guide beyond the North End neighborhood for a leisurely stroll through some of Boston’s best markets and green spaces. You’ll begin the second part of your journey back at the Aquarium “T” Station where we’ll meet more members of the group. From the Harbor, we’ll continue past the Rose Kennedy Greenway.

Pass By: Marriott's Custom House, 3 McKinley Sq, Boston, MA 02109-2609

See State Street and the historic Custom House Tower, the city’s first skyscraper.

Pass By: Faneuil Hall Marketplace, 1 Faneuil Hall Sq Quincy Market, Boston, MA 02109-1604

Then, your guide will lead you toward the famous Faneuil Hall and Quincy Market.

Pass By: Quincy Market, 4 S Market St, Boston, MA 02109-6201

In downtown Boston

Pass By: Old State House, 206 Washington St, Boston, MA 02109-1702

We will 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?

Pass By: Downtown Crossing, Washington Street, Boston, MA 02111

A short trek through Downtown Crossing

Pass By: Old City Hall, 45 School St, Boston, MA 02108-3206

And past Old City Hall

Pass By: King's Chapel Burial Ground, Tremont Street King's Chapel, Boston, MA

We will take you to one of the most historic places in the country, King’s Chapel Burial Ground and King’s Chapel.

Pass By: Massachusetts State House, 24 Beacon St Beacon Hill, Boston, MA 02133-1099

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, designed and built by famous federalist architect Charles Bulfinch in 1798. Outside the State House, take in the views of modern Boston, including the skyscrapers of Downtown, the Financial District, 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.

Pass By: Boston Public Garden, 4 Charles St, Boston, MA 02114-4602

Finally, we’ll arrive at the beautiful Boston Public Garden, one of Boston’s favorite green spaces, where you’ll see locals walking the dogs, playing with the kids and enjoying lunch in the shade.

Activity Details
Discover the local side of Boston’s most popular neighborhood, the North End.  Visit Boston’s most revered church and snack your way through the neighborhood, tasting meats, cheeses, fresh bread, pastries, pizza and cappuccino.  Continue along the Freedom Trail and beyond and experience modern Boston through the city’s incredible history.  From the iconic Boston Harbor,  into the heart of beautiful Beacon Hill, join your local guide on an experience that connects you to the Boston of old and new.
Departure & Return
Departure Point222 State St, Boston, MA 02109, USA Departure Time10:00 AM
Return4 Charles St, Boston, MA 02108, USA
What's Included
  • Local English-speaking guide
  • Snacks - A variety of food samples such as fresh bread, pizza, and pastries
  • Entrance fee to the historic church (or equivalent alternative)
  • A surprise local treat
  • Tips/gratuities for your guide
Additional Information
  • Confirmation will be received at time of booking
  • Wheelchair accessible
  • Entrance to the Massachusetts State House requires a government ID and all guests must pass through metal detectors. The State House is open on weekdays only, we will find alternate sites to visit on weekends.
  • In the event of a site closure, we will do our best to replace it with a similar alternative.
  • This is a child-friendly tour. Children between the ages of 6 and 11 inclusively are permitted on this tour at the rate listed above. Please select ‘child’ above when booking. Children under the age of 6 are permitted to join this tour free of charge. Please inform us at the time of booking if you’ll be bringing a child under the age of 6.
  • We can accommodate vegetarians and other dietary restrictions. Please notify us in advance if you have any dietary requests. You can do so in the ‘Additional information’ box at checkout.
  • Small group of a maximum of 12 people.
  • Near public transportation
  • Transportation is wheelchair accessible
  • Local Impact: How you will help the local community by joining this tour: The Food to Freedom Tour is environmentally friendly because unlike many of the tour companies in Boston, you walk as opposed to using buses or other vehicles.
  • In the morning when you are in the famous North End, all of the food stops are 100% owned and run by locals, ensuring that local people benefit from tourism to their city. So any inclusions on the tour and additional purchases you make will directly benefit the local community.
  • You also stop at a couple of world-famous churches which are as much a part of Boston (and America's) history as you can get. Both the Old North Church and King's Chapel are non-profit organizations that work hard to educate school children and adults on American history and colonial life. By paying an entrance fee, you are helping to maintain the church and their work.
  • Most travelers can participate
  • This tour/activity will have a maximum of 12 travelers
  • Social distancing enforced throughout experience
  • Guides required to regularly wash hands
  • Paid stay-at-home policy for staff with symptoms
  • Contactless payments for gratuities and add-ons
  • All tours follow the latest local health authority advice, including mask usage and social distancing. Urban Adventures has received the World Travel and Tourism Council’s Safe Travels stamp, which recognises companies that have adopted health and hygiene global standardised protocols.
Cancellation Policy
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Traveler Reviews

Average based on 50 reviews.

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  • We had a great experience with Bob as our tour guide. One of my favorite things about Urban Adventures is their dedication to keep groups small (12 max). We felt like we had our very own personal tour guide to learn about Boston. I highly recommend the tour for this fact alone. I have been on similar tours in other cities by different operators with no maximum and the experience is definitely not as fun.

    Here is what you need to know before you book this particular tour:

    - The first half of this tour is of the North End and includes food samples. You get samples of freshly baked bread, a cappuccino, cannoli, a piece of Italian sub, a slice of amazing Sicilian pizza and at one of the final stops a cold beer. The food is outstanding and really filling. They don't provide a sit-down meal, but you will be full!

    -The second part of the tour takes us along of the rest of the Freedom trail. You get admissions to Old North Church along with your tour. This part of the tour is excellent and you will learn a lot about Boston's history, and really the history of our country.

    Be Aware:
    -The tour can run much longer than 5 hours (ours was about 6.5 hours). You are walking and standing almost the entire time. Wear comfortable shoes and bring water. We walked about 5 miles.
    -You can leave the tour at any point, don't feel pressured to stay until the end, especially if you have plans. We ended up really late to our next scheduled activity.
    -This tour ends in a different location from where the tour begins. The tour guides are kind to help you find your way back if needed. We were able to take the T back.

    Overall, this tour is worth every penny. In fact, I think it's underpriced for the value you receive!

  • The food was delicious! Our guide, Conner was very knowledgeable and we learned a lot from him. I highly recommend this tour!

  • Sully is the best tour guide we’ve ever had; his knowledge of Boston’s history was amazing. As first-time visitors we couldn’t have asked for a better tour of the North End. And the food great!

  • Dillon was great. He is knowledgeable and enthusiastic. We did the 5 hr tour and enjoyed the authentic foods and all historic walks. Highly recommend.

  • I've always wanted to see Boston's North End and this tour with Bob Hornstein didn't disappoint. Bob took us to all the important stops and guided us through the very best tastes of Italian food and drink along the way. He made the trip extra special by sharing his personal experiences, stories, and recommendations. Highly recommend this trip!

  • Excellent tour, we highly recommend it. Friendly, knowledgeable guide.
    Overall great experience.
    Food was delicious and not at your usual tourist traps.

  • Our tour guide (Jack) was fantastic. He was informative, witty, down to earth and able to connect with every person on the tour.

  • What a fantastic experience! Our guide Jack had SO MUCH energy and was so personable that he really brought a lot to the tour. I was surprised at all that was included in terms of all the food! I even went back later to the little market to buy some cheese to take home.
    I do many different tours, and each one offers new stories and pieces of history that just add to my vacations as a whole. For anyone visiting Boston, this really is a must. You visit all the key points on the freedom trail and get shown great eateries that are better than the ones with lines down the street.

  • I have to say that the most memorable part of our tour was the attention we received from Sulli. Sulli made a connection with everyone on the tour. He made sure we were good throughout the tour. Sulli is very knowledgeable, affable, and overall a great Bostonian host. He made me want to come back to this wonderful city.

  • Right balance of walking, stopping, eating. Guide was friendly and knowledgeable. Good history and culture overview. All stops were interesting and on point.

  • Sully was great with local knowledge and historical facts. Entertaining and personable. Great host. Felt like we were touring with old friend.

  • Our knowledgeable guide Tim! Excellent and exceptional….. took into account his audience and make it a fun experience

  • Dillon was fantastic. It was like touring with a long time friend. I would suggest this as the first thing you do on North side as it will line you up for what to do and where to go. The only negative is we were left quite a distance from the starting point and had to find our way back. A tour should finish where it starts.

  • Corrine did a fabulous job explaining all the history both with a bit of humor and extensive knowledge. The food was wonderful all provided with the cost of the ticket. Highly recommend this tour.

  • Tour guide, Corrine, extremely talented and very knowledgeable. Good value for the cost but would have enjoyed more food variety

  • Even though it was cold and raining tour day it was interesting and fun! Our guide, Dillion, was awesome! He was entertaining and gave full details on everything wherever we were at. This tour is so worth it! Just be prepared to walk the whole 5 hours with a few stops with sampling some delicious foods and drinks.

  • Tim our guide was great! His knowledge and sense of humor made the tour fun. The food stops he chose were delicious.

  • Sully was an excellent tour guide. He was incredibly knowledgable, kind, and warm. The food was absolutely delicious. I highly recommend this tour!

  • Sully was a great guide . He knew his city took us to off the beaten path places so enjoyable .
    Wear your stretchy pants lots of great food .

  • Corrine and Dave were amazing. Very knowledgeable and flexible. Really liked the freedom trail history and the cannoli and sandwich shop. I think 2 food stops is sufficient vs 4 in that time frame and there should be a beer stop.

  • This was our first trip to Boston. We signed up for the five hour food and history tour to introduce ourselves to Boston. The tour was perfect. We learned so much about the people and history of Boston....where much of our country's ideas and values were born. The food was great and so much of it, I could not eat it all. I loved the cappuccino and cannoli we had at an old coffee shop in the North End. The tour guides were interesting and fun. I also think this tour is good for locals as well to learn details of their city! If you think five hours is too long (it went by fast), you always have the option to leave the tour when you think it is time or if you have other plans. I recommend this tour for food lovers and those interested in history!

  • I loved the North End and all the food tastings. Our guide was very informative. We really covered alot of ground in Boston.

  • My husband and I were the only ones signed up because it was an very cold day. So we had a private tour with Sully. He was amazing! The food was incredible (fresh baked bread, cannoli and cappuccino, Italian sandwich and pizza)! After the food part of the tour we did the history part. It was very informative and Sully was extremely knowledgeable. I would highly recommend this tour!

  • Sully did a great job he was very knowledgeable and friendly and took the time to answer all of our questions

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50 reviews
$104 USD
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