63 Salem St., North End
Admittedly, the line out the door can be a turnoff—but then again, there’s a line for a reason. It moves fast, and these bivalves are worth the wait. Watching the servers shuck hundreds of oysters behind the bar is almost (but not quite) as enjoyable as knocking back a dozen of these briny creatures with generous dollops of mignonette and a crisp glass of sparkling wine. The rest of the menu lives up to the hype—the fish entrées are especially good. The less sophisticated but no less delicious johnnycake—an airy cornmeal pancake soaked in sweet honey butter and topped with sturgeon caviar—is childhood indulgence and grown-up tastes combined; order one for the table.
257 Hanover St., North End
Boston is a city that actually has bakery crawls—and with good reason. Each one of the probably hundreds of Italian bakeries in the city and its surrounding suburbs claims to specialize in one of many Italian pastries. Modern Pastry is no different, other than that there is really nothing modern about its pastries at all. (Note the retro plastic-signed storefront.) Here, the specialty is lobster tails—named for their shell-like shape—or what Italians call sfogliatelle. The pastry is composed of what looks like hundreds of thinner-than-paper, crispy, flaky, butter-painted layers, filled with orange-zest-flecked ricotta. Sfogliatelle are far too labor-intensive to make in your own kitchen, making the excursion to Modern Pastry as necessary as it is indulgent. Only in Boston, parts of Brooklyn, and Campania would you find something so obscurely Italian.
300 Hanover St., North End
Ask any local for a can’t-miss in this city, and they will send you to Mike’s. The bear claws (giant flaky cream-filled pastries) are so good that one goop staffer goes here as soon as she lands at Logan. A family business, the bakery was started in 1946 by Michael Mercogliano (that’s the Mike in Mike’s Pastry), who arrived from Italy when he was only twelve. Nowadays, it’s run by Mike’s stepson. The team of bakers churns out thousands of the most delicious cannoli you’ll have outside (or possibly inside) of Italy, all packaged in beautiful blue-and-white boxes wrapped in twine. Flavor fillings are endless—hazelnut, chocolate mousse, expresso, pecan caramel, mint chip, even Oreo, to give you an idea. There are multiple lines, and half the fun is weaving your way from one to the other to make it up top. While the heaped cookie trays and ricotta pie may catch your eye, you (and the rest of Boston) are here for the cannoli.
290-296 Hanover St., North End
Reputedly the first Italian café in Boston and open since 1929, Caffe Vittoria resembles those old-world cafés you find in rural Italian towns. The worn marble floors, the glass display cabinets, and a treasure trove of old coffee machines and espresso makers are reason enough to show up; Vittoria’s is as close as you’ll get to a museum of the development of the modern cup of espresso. This is not the place to order drip coffee. Instead order a cappuccino—and see how it’s really made. Two shots of strong espresso topped with creamy, near-stiff foamed milk, plus a dusting of cocoa. Maybe chase the coffee with a grappa (or vice versa) before looking around.
33 N. Sq., North End
North End is a fun destination for dinner, specifically for Italian food, where your best bet is Carmen Trattoria, which has a lovely, low-key, exposed-brick dining room. It’s a good idea to call ahead for a reservation. If you can, save room and walk to legendary Mike’s Pastry after dinner. The cannolis get all the attention, but the lobster tails are really where it’s at. (Side note: Another popular spot for old-school Italian in Boston is Giacomo’s, which has a location in the North End, as well as one in South End, and a third outside of the city.)
92 State St., North End
This Greek spot has a pretty short menu—they stick to gyros and an excellent Mediterranean salad. The pork loin for the traditional gyro is marinated and stacked on a rotisserie (no horrifying cone in sight), and then sliced on to fresh pita to-order. It’s the kind of place you’ll want to black-book for your next craving. There's a second location Downtown.
236 Hanover St., North End
Thinking Cup's cozy interior is the ideal place to hide out during a freezing nor’easter. The exposed-brick walls and low ceilings create an intimate vibe, and the Stumptown coffee is brewed to perfection. The menu is just the right length (a nice array of pastries and breakfast options, and four to five choices for a sandwich if you're around at lunch), but you really don't need much more than a coffee and a corner table to make yourself at home in here. There are also outposts on Tremont Street and Newbury Street.
Boston Common Coffee Company
97 Salem St., North End
As its name suggests, this place feels like classic Boston. You won't find any fancy décor, but the coffee is really solid and the baked goods are famous in the neighborhood. Stop by on Thursdays, when they introduce new doughnut flavors (although if Boston cream is an option, your decision's already made for you). It's really meant to be a place where people can meet and get work done, so you'll be grateful for the abundant seating options and reliable Wi-Fi. P.S. How could you not love the coffee shop that made cookies shaped like deflated footballs after deflate-gate in 2015? There are two locations downtown: Canal Street and Washington Street.
226 Causeway St., North End
This coffee shop is actually part of a larger co-op dedicated to selling fair-trade goods like coffee, chocolate, tea, and more—it even has a sister restaurant in Seattle and a full-fledged fair-trade business behind it. That humanitarian spirit is embedded in everything it does: It's completely worker-owned, and offers presentations from its farmers and baristas about the coffee. Niceties aside, the coffee is seriously good, and there are usually open tables—it’s an ideal space to cram in a few hours of work before a meeting downtown.