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  • Writer's pictureKatie Wright

Pizza Touring through Boston’s North End

Updated: Jul 24, 2020

Why is it that we rarely ever play tourist in the city we live in?

Boston is one of America’s most historic and scenic cities and I’ve lived here all my life, yet I’ve participated in so few of the ‘touristy’ attractions that draw so many people to visit here.

On the very first day that’s felt like Spring here in Boston, Lewis and I set out to embrace the culture that’s at our very doorstep and join a pizza tour in the city’s North End.

The North End, also known as Boston’s Little Italy, is a maze of tightly woven little streets lined with cannoli shops, the sound of Italian accents and restaurant after restaurant. Some of the shopfront signs are even in Italian, if you let your mind wander it really does feel like a world away.

Here are the highlights of our day as illustrated through my Instagram story:


We met our guide, Sean, at the corner of Hanover Street and Cross Street, near the Tony DeMarco boxers statue and set off on our three hour pizza eating and history learning spree.

Our first stop was Galleria Umberto.


This is why I love food tours: I never would’ve stepped foot in Galleria Umberto if it hadn’t been for this tour.

It doesn’t look like anything special from the outside. And compared to some of the other shops along Hanover street, it wouldn’t have been my first pick, just based on appearances alone. But you know what they say—don’t judge a book by it’s cover—and the same goes for pizza shops.

It turns out Galleria Umberto is an award-winning, time honored establishment with a serious cult following. Galleria Umberto only has six things on the menu and is open until it those items sell out.

Among those items is a classic Sicilian style square pizza slice. Think thick, but somehow not heavy, crust, a sweeter tomato sauce and salty cheese served hot. A great first stop on our journey.


Our second slice was the crowd favorite at newly opened Rina’s. Delicious Napoli style pizzas made to order in under three minutes by the charming Fabio, an Italian import himself.




Our third stop is a tourist’s ‘must not miss’ on a trip to Boston: Regina Pizzeria.


Open since 1926, Regina’s is a family owned business serving delicious brick oven pizza. While there are Regina Pizzeria’s all around Boston, the North End location is the original, and the ‘only one worth going to,’ according to our guide, Sean.

Although it wasn’t an official part of the tour, I couldn’t resist going to the North End without visiting my favorite cannoli shop: Modern Pastry.


It doesn’t get any better than this!


Thank you for a great day Boston Pizza Tours


Planning a trip to Boston? Check out some of my other favorite things to do in the city: 

7 Foods to Try in Boston, USA

Photo Guide: Harpoon Brewery Tour – Boston

A Sweet Afternoon at The Langham Hotel’s Saturday Chocolate Bar in Boston

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