Taking Boston's "Politically Incorrect" Walking Food Tour
Experience Boston's North End like never before with a politically incorrect food walking tour filled with history, humor, and delicious eats.
For my entire life, I have lived in the New England region of the Northeastern United States, and most of these cities feature "little" enclaves of immigrant populations. I grew up in Central Connecticut where Polish and Puerto Ricans have settled quite nicely. Portuguese immigrants have settled for several generations along the Massachusetts coastline and in Rhode Island. Along the Massachusetts coastline and in Rhode Island, Portuguese immigrants have made their home for several generations. Boston is famously known for its waves of Irish immigrants who have settled there over many decades and generations. The North End of Boston exemplifies this, boasting a rich history with its narrow, winding streets adorned with historic buildings, many of which trace back to the 18th and 19th centuries, showcasing the architectural styles of those times. As the city expanded, the North End evolved into a cultural melting pot, especially during the immigration surges of the 19th and early 20th centuries, when Italian immigrants began to arrive, bringing their vibrant traditions, delicious cuisine, and lively community spirit. Over the years, the North End has undergone a renaissance, particularly in the 1990s and early 2000s. The arrival of new residents, including young professionals and families, ignited a revitalization of the neighborhood. This demographic change led to rising property values and a surge of new businesses, from trendy cafes to upscale dining spots. The historic architecture of the area was preserved and restored, enhancing its charm while keeping its cultural heritage intact. One thing that remains unchanged in the North End is the food. Chain restaurants are nowhere to be found, now or in the future. While the longtime residents of the neighborhood have learned to interact with the new arrivals, they take pride in their heritage. This blend of authentic Italian-American tradition and diverse food offerings inspired me to seek out a unique food tour - one led by a truly colorful local!
What Makes This Food Tour "Politically Incorrect"?
I booked this walking food tour on an early summer Friday at around 2:30pm. The ticket instructed us to meet at the North End Branch of the Boston Public Library. However, since the tour operates independently of the library, the actual meeting point is outside in the alcove at the front of the library. This area is shaded, providing a pleasant respite from the summer sun. There are no signs to guide you, and the tour may start a bit late. From my conversation with another attendee who had been on this tour before, I learned that this is quite common. When you notice a small group gathering in the alcove, that’s your cue that the tour is assembling there. After about 15 minutes, an older Italian-American man arrives. His name is Anthony Gesualdi and he's about as old school as it gets. With slicked-back graying hair and a reddish complexion, he shows up holding an unlit cigarette and wearing a black t-shirt that humorously lists the “requirements” (I found the list amusing, as it mostly covered general tour etiquette). Anthony used to own a restaurant but has shifted to conducting tours in his later years. After introducing himself and openly expressing his frustrations with Viator, he began to share the history and transformations of the North End of Boston, which was once a vibrant Italian neighborhood but has undergone significant gentrification, much to the dismay of long-time residents. On a personal note, I must admit it felt a bit surreal for me because Anthony bore a striking resemblance to my cherished paternal grandfather, both in appearance and demeanor, whom I lost unexpectedly when I was just 12 years old.
What You Will Experience on the Politically Incorrect North End Food Tour?
After learning about the history of the North End, we moved on to the walking food tour. All of the food shown below is included in the tour price. I took plenty of pictures of the food, and that will tell the story! Needless to say, it's a lot of walking in a small area, so wear some comfortable shoes!
Our first stop was just down the street at Polcari's Coffee for some fantastic Italian ice.
Our next stop was Monica’s Mercato Grocery for sandwiches. We had an excellent Italian sub with fresh thin sliced cold cuts, balsamic vinegar and true fresh baked bread. Even my small sample size was quite filling!
In between the food, Anthony shared tales from his childhood in the North End, especially recalling a visit to 98 Prince Street, the location of the Boston Mob's headquarters, where the notorious gangster Whitey Bulger betrayed the Italian mob.
Our next stop was at L'Osteria Ristorante for a couple of raviolis, which feature pillowy soft ricotta and are served in a bolognese sauce. Really tasty, especially when paired with a glass of Chianti (for a little extra cost). Sadly, I don't have a food pic for this one. I loved it, so trust me on this!
Monica’s Pasta Shop was the next move where we had some really well made arancini. Absolutely delicious!
Quattro featured amazing brick oven pizza, with that coal char on the crust, and we had slices of a white pie, that had that crust that’s both chewy and crunchy.
In the end, we explored a few additional spots to savor dessert-focused dishes, wrapping up our meal with espresso gelato that reminded me of an 'espresso float.' While I'm usually not a fan of desserts, I truly appreciated this as our final stop!
Should You Take This Tour?
Overall, the tour was great. Mr. Gesualdi is a character and is a very nice man, but also a man set in his ways. He’s crude as well, when he walked us over to our first stop at Polcari's, he knocked on the window and waved his middle finger to the owner. Of which the owner of Polcari's did the same. I thought it was hilarious and it’s meant to be funny, so definitely have a sense of humor and you’ll get along just fine. Also, he uses very colorful language, so again, know what you’re getting into. With that being said, he’s very gregarious, talks with his hands and his arms and is a real authentic Italian-American guy. You’ll get long talks and stories about the neighborhood and you’ll get the history of the North End of Boston. He also made an excellent point that many of these tour companies are staffed with college students who aren’t from the neighborhood and are utilizing a script. He mentioned many of these tour companies are corporations. It’s a great point, and it’s why it’s important to do your research. With Anthony, as crude as he is, you’re still getting an authentic experience, and it’s well worth it - even if it might make you a little uncomfortable.
Boston's "Politically Incorrect" North End Food Tour is a 3 hour guided walking tour that runs daily usually in the midday, and two tours on Saturday usually in mornings and again in the afternoon. Tour sizes will often vary depending on the time of year, and the tour runs daily from Spring until Christmas, and on weekends only from early January to May. Private tours are also available and can booked directly on the website. You can book a tour on their website, or if you want to help support Red Solo Traveler, you can book through Viator using my link below or my link here!
Anthony was also featured on a TV report and is somewhat of a TikTok star. I only know this because he mentioned it! Check out the video from the Boston Web Group below:
Have you been on this tour? Would you take the politically incorrect food tour? Discuss below in the comments!