A guided walking tour featuring stops at iconic local eateries for Italian subs, pizza, ravioli, pastries, and desserts, with historical insights.
Hear firsthand stories from Anthony about growing up in the North End, including neighborhood history and unfiltered, humorous anecdotes.
Interact with longtime residents and shop owners, offering a genuine glimpse into Boston's Italian-American community.
Join a lively group experience with up to 40 people, ideal for visitors seeking social fun and shared laughs.
Book directly through Anthony to avoid third-party fees and ensure timely support for your tour planning.
Anthony is a wonderful story teller that makes you fall in love with North Boston and the close knit community of Italians that made it home for decades. Not only do you get to experience excellent food, but you get to hear the history behind the families running the shops and get a taste of local culture. Anthony is so enduring, you love him immediately. The food was absolutely delicious, he doesn’t skimp on the sizes and you’ll leave feeling full. It was well worth the time and money. I’ll do it again the next time we come.
The tour guy is that one uncle we all have and love but dont want to introduce to friends 😂. He actually grew up in the North End and hearing stories about life there in the 70’s was so interesting. He cusses and smokes and don’t look too close at his shirt 😂😂😂. We got to try some of the popular spots and some I never would have known about. 11/10 I highly recommend.
⭐️⭐️⭐️⭐️⭐️ Our group had an awesome time on the tour with Anthony! It was my first time in Boston, and as an East Coast Italian myself, I was on a mission to find real North End Italian food — not the touristy stuff. Anthony absolutely delivered. You can tell he’s passionate about the neighborhood he’s called home his whole life, and he takes you to the best local (not corporate) spots that you probably wouldn’t find on your own. The food variety was fantastic, seriously, come hungry. But if you’re a “Karen” who’s easily offended, maybe sit this one out 😂 Anthony keeps it real and makes the whole experience hilarious and informative. My only tiny critique: the tour group was pretty big (around 40 people), so a few stops felt a bit cramped, but it was a gorgeous fall Saturday so many people were out and about in the city. All in all, highly recommend this tour if you’re after amazing food, great stories, and plenty of laughs. Thanks, Anthony, for a great day in Boston! 🍝
One of the Best Values in Boston! If you’re visiting Boston and want a tour that blends incredible food, authentic history, and a ton of laughs, look no further than The Politically Incorrect North End Food Tour. Our guide, Antony, grew up in the North End, and you can feel his love for his neighborhood in every story he tells. His humor, honesty, and deep knowledge of the community made this tour stand out from anything else we’ve experienced. We sampled some of the North End’s most iconic foods: Italian subs at Monica’s Mercato, legendary pizza from Regina’s, homemade ravioli at L’Osteria, fresh pastries at Bricco Salumeria, and even a refreshing lemon slushie at Polcari’s Coffee. We ended the tour with a heavenly affogato at Dolce. Every stop came with not just amazing flavors but also history and local backstories you simply wouldn’t get on your own. A few notes: this tour is not for everyone. Be ready for some F-bombs and strong language — it’s part of the charm, and exactly why it’s called “politically incorrect.” If you’re easily offended, this may not be the tour for you. But if you’re up for humor, candor, and a guide who keeps it real, you’ll love every minute. Insider tips: • Book directly through Antony — not through Viator or third-party sites. They tack on huge fees and delay paying him for weeks. • Come hungry and wear comfy shoes! You’ll be walking, eating, and laughing your way through Boston’s Little Italy. • Book early in your trip — you’ll want time to circle back to these spots on your own. This tour is hands-down one of the best values in Boston. I honestly can’t wait to plan another trip back just to do Antony’s tour again and revisit all these incredible places.
This was easily one of our favorite tours of all time. Anthony, the owner and guide, is the real deal—a true Boston Italian whose personality and storytelling make this experience unlike anything else out there. “Politically incorrect” isn’t a gimmick, it’s exactly who he is. If you’re a Karen, this tour isn’t for you. But if you appreciate authenticity, you’ll laugh harder and enjoy yourself more than on just about any tour you’ve ever taken. As fellow tourism business owners, my wife and I couldn’t stop talking about how free and natural Anthony gets to be with his customers. His style could never be taught in a hospitality class, and it will never be replicated. You have to experience it while he’s still here doing it, and while his lifelong friends continue running the few remaining mom-and-pop restaurants in the neighborhood. The food itself was outstanding, but what makes this tour truly special are the genuine interactions with locals and Anthony’s firsthand stories about how life used to be in Boston’s North End. This isn’t just another food tour—it’s an unforgettable glimpse into the history, culture, and community of one of Boston’s most iconic neighborhoods. Reviews can’t do it justice. Just go.

Authentic Boston Italian food tours with unfiltered stories and laughter—no Karens allowed!
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Experience Boston's historic North End like a local with Anthony, a lifelong resident who blends incredible Italian food with hilarious, politically incorrect storytelling. This tour takes you beyond the tourist traps to family-run shops and restaurants, serving up delicious subs, pizza, pasta, pastries, and more while sharing the neighborhood's rich history and culture. Perfect for those who appreciate authenticity, humor, and a genuine taste of Little Italy.
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