From Food to Freedom Trail
Boston, USA
From USD 99.00
Office phone number: + 1 617 539 8271
From Food to Freedom Trail
Boston, USA





Culture shock rating
Worried we’re going to shock your senses? Relax! We believe part of the fun of travel is immersing yourself in the destination and its culture, meeting the people, and learning what makes the place tick. We’ve got a wide range of tours with something for everybody. The cultural shock rating ranks how different the experience is from most Western cultures. But no matter the level, don’t worry, you’ll have a local, in-the-know guide with you every step of the way.
Low
Consider these tours your 101 intro to a place. Transportation might be private or a very comfortable public option, and the activities are usually visits to iconic sites and locations that are familiar to most Western cultures – but that will still give you fantastic insight into a destination.
Medium
Expect to rough it for parts of this tour, whether that’s on a packed public bus or in a local market off the tourist trail. There might be a few language barriers or unfamiliar cultural customs, and you’ll get an experience different from what you're used to at home.
High
You're out there in the global community! We’re going to take you down streets you’d rarely explore on your own, introduce you to local customs and languages, and take you for a ride in whatever transport is available. Get ready to take it as it comes, whatever comes. There might be a shock, but oh man, it’s worth it.

Physical rating
Worried our tours are too tough? Relax! From leisurely strolls to muscle-burning treks, we’ve got a wide range of tours with something for everybody. The physical grading gives you an idea of how much huffing and puffing you can expect on the tour.
Low
Slow and steady is all you need here. These tours have very limited physical activity, such as walking relatively flat streets, sites, or markets, and climbing in and out of the transport provided.
Medium
Not too hard, not too soft, these tours are just right! You can expect a bit of physical activity, but nothing overly challenging – perhaps walking up and down hills, riding a bike for up to 30 kilometers along mostly flat terrain, or jumping in a kayak for a gentle paddle on flat water.
High
Get ready for a workout! These tours are our most challenging and involve intense walking, hiking, kayaking, swimming, or bike riding. You could be making steep climbs by foot or pedal, or working your core in the water. We recommend you have a good level of fitness to join this tour.
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Tour snapshot
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.
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Highlights
- Stroll past some of the most historic locations in Boston’s oldest neighborhood
- Join your local guide for a fun-filled journey on and off Boston’s famous Freedom Trail
- Learn the modern impact of Boston’s most iconic historic sights
- Take in the beauty of the architecture and quaintness of Beacon Hill
- Enjoy a beer and some tasty snacks at some of our favorite local haunts
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.
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Schedule details
- Duration: 5 hours
- Meeting point:
The Aquarium “T” Station (Outside, in front of the Long Wharf Entrance – Northeast Corner of State St. and Atlantic Ave.) 222 State Street, Boston, MA 02109
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- Find the exact meeting point with what3words:
- Starting time: 10.00 AM
- Ending point:
Boston Public Garden (or nearby), 4 Charles St., Boston, MA 02116
Language: English
Inclusions: Local English-speaking guide, a variety of food samples such as fresh bread, pizza and pastries, entrance fee to the historic church, one beer (or non-alcoholic beverage of your choice).
Exclusions: Additional food and drink, souvenirs, tips/gratuities for your guide.
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, with views of the harbor, East Boston and historic wharfs lining Atlantic Ave. We’ll make our way to the heart of the North End, with views of some of the most historic sites and properties in the neighborhood, some dating back to the late 1600s and 1700s.
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 at their finest and freshest.
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. Here, you will have a chance to enjoy your choice of a classic cappuccino, espresso or tea.
As you let the caffeine kick in, your guide will go back in time into North End history. 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.
After church, we’ll dive deeper into the local side of the North End. 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. Hopefully there will be a chance to meet and chat with the area’s best bakers, if we catch them at a quiet moment.
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, State Street and the historic Custom House Tower, the city’s first skyscraper. Then, your guide will lead you toward the famous Faneuil Hall and Quincy Market, which both boast stunning views.
Moving into the heart of Downtown Boston, 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? Ask your expert guide about that one!
A short trek through Downtown Crossing and past the Old City Hall will take you to one of the most historic places in the country, King’s Chapel Burial Ground (city’s oldest burial ground) and King’s Chapel (the first Anglican church in the country). Whenever possible, your guide will take you inside King’s Chapel, the first church in the USA to have a pipe organ. If we’re lucky, we might just get to hear it being played.
Somewhere along the way during this tour, you’ll have a chance to rest your legs and enjoy a refreshing local beer. Your guide will choose among some of the most historic, quirky and hidden local bars and taverns in the area.
On most weekdays, you’ll have a chance to see the government at work (or not) 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. Get out your cameras — this neighborhood is one of the most photogenic in the city.
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. Your guide will point you in the right direction, and will help with any and all recommendations for great things to do in Boston that evening and beyond.
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Additional information
Inclusions: Local English-speaking guide, a variety of food samples such as fresh bread, pizza and pastries, entrance fee to the historic church, one beer (or non-alcoholic beverage of your choice).
Exclusions: Additional food and drink, souvenirs, tips/gratuities for your guide.
Your Trip: For your Urban Adventure you will be in a small group of a maximum of 12 people.
Confirmation of booking: If you have your voucher, your booking is confirmed. We'll see you at the start point. Get in touch if you have any concerns or require more information via the email address or phone number (business hours only) on your voucher.
Additional Information: 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.
Closure of sites: In the event of a site closure, we will do our best to replace it with a similar alternative.
Child Policy: 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. You can do so in the special request box on the checkout page.
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Dietary Notes
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, or by emailing us at info@bostonurbanadventures.com.
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Local contact
Office phone number: + 1 617 539 8271
Email address: info@bostonurbanadventures.com
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