Boston Food & History: Pizza, North End & Freedom Trail
Overview
Available languages
5 hours
Mobile ticket
Uncover Boston’s best-kept secrets on a walking tour that blends history, culture, and flavor. Wander through the iconic North End, tasting fresh bread, pastries, pizza, and a classic Italian deli sandwich. Visit a legendary church, stroll the Freedom Trail, and soak in stunning views from Boston Harbor to charming Beacon Hill. With a local guide leading the way, experience the Boston you’ve always dreamed of—authentic, delicious, and unforgettable.
Additional Info
Wheelchair accessible
Public transportation options are available nearby
Transportation options are wheelchair accessible
Suitable for all physical fitness levels
Can this tour accommodate dietary requirements? Absolutely. We can cater for vegetarian, vegan, and gluten-free options. Please notify us at least 24 hours before the tour start time if you have any dietary requests. While we do our best to accommodate these needs, substitutions may not be identical to the original menu items.
Is this tour environmentally friendly? Unlike many Boston tours that use buses or other vehicles, this experience is entirely on foot—making it a more sustainable choice.
How does this tour support the local community? In the North End, all food stops are 100% owned and operated by locals, ensuring your visit directly benefits the community. Any inclusions and additional purchases you make help support local businesses.
Do we visit any historic sites? You’ll stop at the world-famous Old North Church, a non-profit organization dedicated to preserving American history and educating visitors. Your entrance fee helps maintain the church and its educational programs.
Can the route or inclusions change? We reserve the right to adjust the route and places visited. Food inclusions may vary depending on availability on the day.
Is the tour suitable for all fitness levels? Yes, but please note the tour involves approximately 8 km (5 miles) of walking.
Is this tour child-friendly? Yes! Children under the age of 6 can join this tour free of charge.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What To Expect
Greenway Carousel
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. Your experience begins at the lifeblood of Boston, the Boston Harbor. Walk through a scenic waterfront park, with views of the harbor, East Boston and the 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 early 1700s.
Rose Fitzgerald Kennedy Greenway
We will pass by the Rose Fitzgerald Kennedy Greenway, a linear park located in several Downtown Boston neighborhoods. It consists of landscaped gardens, promenades, plazas, fountains, art, and specialty lighting systems.
What‘s Included
Indulge in one food and drink stop with a hot Italian beverage and pastry in Boston’s North End
Walk Boston’s famous Freedom Trail and uncover stories of the American Revolution
Enjoy three food stops featuring fresh North End bread, pizza, and an Italian deli sandwich
Visit the historic Old North Church, a Freedom Trail icon (entry when available)
Get tips on what else to see, do and eat during your stay
Savor a local surprise treat handpicked by your guide for an authentic Boston experience
Explore Beacon Hill’s charming red-brick streets and classic Boston architecture
Take in scenic views of Boston Harbor and the Rose Kennedy Greenway
Tips/gratuities for your guide
Additional food and drink
Options
Food & History Tour
Reviews
1,764 reviews
Total reviews and rating from Viator & Tripadvisor
The Best Foodie and Historical tour in Boston
frankiecD2221KU,,Dec 27, 2025
- Review from Tripadvisor
5.00This tour is amazing. Olivia is our tour-guide. Overall, She is super friendly, fun and very knowledgeable, which makes me having a wonderful and unforgettable day in Boston. The first part is the foodie tour, which we have chances to understand the North-end Italian community and the local food. All stops are delicious and representative. Olivia manages the time and the related food arrangement well, so we have sufficient time to try the food and understand the context in each stop. The best part is that we can interact and exchange thoughts after trying the food, given that we come from different parts of US and around the world. Olivia also provides useful recommendations on different restaurants for us to try in our own time. Part of the restaurants and shops we go are super hidden-jams, which I never expected! The second part is the freedom trail. Olivia introduces each stop with simple, fun and insightful stories, which are fitted and customised into our diversify backgrounds, so we can all understand the importance and story behind easily and quickly. You always have chances to ask questions. The best part is that Olivia always provides the fun facts in each stop and shares what she (as a Boston local) think & proud of, so this makes each stop colourful, reflecting, and memorable. Olivia makes the whole trail tour super interesting. It never gets bored and you will definitely laugh & treasure a lot from Olivia’s. Given that it is the cold winter, the coffee stop is also very helpful. Everything is well-planned and organised perfectly by Intrepid and Olivia. I am so thankful and glad that Olivia to be our tour guide. I definitely recommend all to join the tour with Intrepid andOlivia to experience the delicious, historic and dynamic parts of the Boston.
Boston’s little Italy Food Tour
catherinef108,,Dec 27, 2025
- Review from Tripadvisor
5.00Olivia was a wonderful guide for us. We learned a lot. The food experience was very nice too. We were a small group on a day in winter after a snow the night before. It was all good.
This tour was...
Darian H,,Dec 18, 2025
- Review from Viator
5.00This tour was exceptional. The guide was extremely knowledgeable. The food and drinks were excellent!
Wonderful Tour With Conor
metay edwards,,Dec 13, 2025
- Review from Tripadvisor
5.00Awesome tour with Conor! I learned a lot of new things about Boston history and had so much fun. He was so pleasant and welcoming and it was a wonderful experience!!
Fabulous tour and guide!
nanmacari,,Dec 13, 2025
- Review from Tripadvisor
5.00What a great tour! From Connor, our tour guide to the history he shared it was perfect! I will definitely take more tours and hope to have Connor as our guide again!
Best Boston tour with the best guide!
demetrae2020,,Dec 13, 2025
- Review from Tripadvisor
5.00BEST BOSTON TOUR EVER WITH OUR TOUR GUIDE, CONNER!!! We had such an amazing day touring the North End and trying so many delicious foods and seeing so many sights in Boston. Even on a cold December day, we had so much fun exploring the North End and hearing all the interesting stories and facts from our amazing tour guide, Conner. He was so knowledgeable on all Boston facts and kept us smiling and laughing all day. I would recommend Conner’s tour to everyone who loves history, walking and good food!! It was a fabulous day.
Awesome experience
christophebartlett,,Dec 4, 2025
- Review from Viator
5.00I had an awesome time. The tour guide was very efficient and kind. I recommend this tour to anyone who doesn’t mind walking long distances. lol! Awesome experience. I loved it!
Fun and enriching
Cruiser67232727867,,Nov 25, 2025
- Review from Tripadvisor
5.00It was an excellent day, I learned a lot about pop culture, history and local architecture, as well as the varied and delicious local food that I consider an important part of sightseeing, I loved it!!!
Now This A Tour!
shaunb539,,Nov 23, 2025
- Review from Tripadvisor
5.00My wife and I have been on a handful food tours now as we've found them to be a great way to get to know a city. This will definitely go down as one our favorites. Nabil did a fantastic job, providing a fun, insightful, and humorous experience throughout. I really appreciated his stories and attention to detail at the various locations. This tour was very well thought out, the food was amazing, and the history of the city was fascinating.
Great introduction to Boston food and history
Mark8888,,Nov 23, 2025
- Review from Tripadvisor
5.00The 5 hours flew by and was nicely paced. Despite some rain we had all learned a lot, saw a lot and ate a lot. Guide Nabil was insightful and entertaining. Had 2 good coffees, pizza, a great sub and of course cannoli (was it the best - who knows but that’s a huge debate in Boston). Thoroughly recommended.
From US$100.96
Want a private experience? Upgrade to a private tour
Related Experiences
Operated by Intrepid Urban Adventures - USA