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Dining in the North End

As the city's oldest residential area, the North End contains some remarkable Revolutionary history (including Paul Revere's home)—and some really remarkable Italian food.

Though it's been the center of Italian culture in Boston since the early 20th century, the North End was cut off from the rest of Boston for more than five decades by the construction of an unsightly elevated highway. As part of the Big Dig project in 2007, the highway was torn down, and the young professionals who work in the nearby Financial District raced to move into the neighborhood.

Today the North End remains largely residential, with an interesting mix of twentysomethings and Italian grandpas. The narrow streets can be eerily quiet during the day but then transform into vibrant meeting places come evening, as couples take advantage of the romantic opportunities afforded by the neighborhood's small, rustic restaurants. On summer evenings there's a good chance you'll encounter a street fair celebrating a saint's feast day, filled with food booths selling cannoli, fried dough, and sausage sandwiches.

North Tour

To eat like an Italian, you've got to know your sfogliatelle from your amaretti. Local foodie Michele Topor schools visitors on the "right" kind of olive oil and the primo places to buy Italian pastries during three-hour tours with North End Market Tours (6 Charter St. 617/523-6032), which get off the beaten Hanover Street path. The $50 tour includes a few sample noshes.

A North End "Course Crawl"

The neighborhood is so densely packed with authentic Italian eateries (there are more than 85 lining just a few blocks) that it's nearly impossible to suggest only one. Instead, we recommend embarking on an evening-long "course crawl" to enjoy a variety of the North End's flavors while severely challenging your stomach capacity.

In summer, start with a drink at Ristorante Fiore (250 Hanover St. 617/371-1176), which has one of the city's best roof decks and a similarly impressive wine list heavy on the Tuscan varietals. Then swing by Neptune Oyster (63 Salem St. 617/742-3474) for a batch of its namesake crispy oysters served with pistachio aioli as a starter, before crossing the street to Terramia (98 Salem St. 617/523-3112), where the huge sea-scallop ravioli comes dressed in a lobster mascarpone cream and the gnocchi is accented by white truffle oil.

True Italians make room for secondi, or a second, meat-based course. You can't go wrong with Prezza's (24 Fleet St. 617/227-1577) wood-grilled venison with roasted cipollini onions, salsify, and red wine sauce, or try the seared salmon fillet at the broom closet-sized Pomodoro (319 Hanover St. 617/367-4348).

Before you can succumb to a carbohydrate-stuffed stupor, you need dessert—but most North End restaurants don't serve it. That's because everyone buys cannolis at local bakeries instead. Stop by Modern Pastry (257 Hanover St. 617/523–3783) and Mike's Pastry (300 Hanover St. 617/742–3050), the two main North End dessert shops, to conduct your own cannoli taste test. Located across Hanover Street from each other, both shops have around-the-clock lines snaking out the door. Modern's cannoli are smaller, more delicate, and flakier than Mike's counterparts, but as for the preference, it's up to you. If you're ricotta-averse, the two bakeries also serve whipped-cream versions, as well as lots of other treats, from gelato to biscotti and marzipan.

Coffee Talk

Café culture is alive and well in the North End. Caffe Vittoria (290–296 Hanover St. 617/227–7606), established in 1929, is Boston's oldest Italian café. With four levels of seating, three bars that serve aperitifs, and one massive, ancient espresso maker, this old-fashioned café will make you want to lose yourself in these surroundings. At Caffé Paradiso (255 Hanover St. 617/742–1768) soccer pennants hang from the rafters and the TV plays only European futbol matches—two sure signs of authenticity. Caffe dello Sport (308 Hanover St. 617/5235063) is an Italianate version of a sports bar, with two wide screens transmitting live soccer; order espressos, cordials, and gelato. If you're not able to kill a whole afternoon sipping cappuccino, stop by Polcari's Coffee (105 Salem St. 617/227–0786), selling dried goods by the pound—coffees, teas, herbs, and spices displayed in antique brass bins.

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