14. The North End
It has the history, seeing how people have lived there continuously since the 1630s, and it’s been predominately Italian for well over 100 years. Until the Dig was completed, the Central Artery blocked it off from the rest of Boston, isolating the North End but also creating an even more tightly knit Italian-American community where food really, really mattered. When I was little, it was the only neighborhood I really knew about, because we’d always go eat next to Paul Revere’s house at Florence’s before Celtics games. It’s closed now, but plenty of the red sauce legends live on, like Giacomo’s, Pomodoro, and Mama Maria, next to the essential pizza spots (Galleria Umberto, Regina, Ernesto’s), and the infamous cannoli rivals (Mike’s and Modern). Not into Italian food? No problem (well, sort of a problem, but whatever), oyster bars like Neptune Oyster Bar and coffee houses like the Thinking Cup can keep you occupied. And all of this within basically five blocks. Che è impressionante, indeed.