An urban clam shack with incomparable views of the skyline, the restaurant sits on Fort Point Channel across from the financial district and has an authentic New England atmosphere, complete with gruff service, rough picnic tables and a smattering of tough locals. On a warm afternoon or evening, this is a classic spot to pass the time over messy lobster rolls and ice-cold beers. In the summer, some diners arrive by boat, the small sails contrasting with the soaring skyscrapers across the channel. But even in the winter, the Crab remains open. When the wind dies down and the sun comes out, a February afternoon may suddenly feel like springtime.

Legal Seafoods is a Boston institution, and while there are now many locations (still mostly in Massachusetts) a trip to Boston deserves a trip to Legal Sea Foods. It’s nothing fancy, and diners looking for a fine-dining experience should steer clear, but it’s about as Boston as it gets. Legal’s has been voted “Boston’s Most Popular Restaurant” by Zagat every year since 2003.  The clam chowder is legendary and has apparently been served at every presidential inauguration since 1981.

Mr. Bartley’s began serving burgers at its Mass. Ave. location in 1960, and a meal here has been a Harvard tradition since. To this day, the line for one of the rickety tables often extends down the block, composed of locals and tourists awaiting the chance to choose from cheekily named selections like the John Kerry (“he voted for this burger before he voted against it”), the Larry Summers (“the Harvard president—women can eat this, too! burger”) and the Dick Cheney (a bacon cheeseburger described as “a heart beat away”). The walls are covered in Boston memorabilia, and noise levels rise to shouting as patrons cram themselves into the limited seats and the harried waitstaff rushes from table to kitchen. Although no alcohol is served, the restaurant’s frappes, New England vernacular for milkshakes, are almost as legendary as its burgers. Come armed with patience, a horse-sized appetite and cash, as Mr. Bartley’s does not accept credit cards.

Joanne Chang has quite an empire in Boston, and it is only growing. Along with this popular Chinese spot, Chang has several Flour outposts in the city and two cookbooks featuring her most popular recipes.  Myers + Chang (the Myers comes from her husband Christopher Myers) is not your traditional Chinese restaurant; in fact, its dishes are closer to hipster Asian cuisine. From the hot pink dragon decals on the walls to the delightful sweet and spicy chicken and waffles, Myers takes creativity to another level. The food is always fantastic, the drinks are pungent and exotic, and the scene is trendy, friendly and fun.

This little gem in the South End is perfect for grabbing a quick latte and sweet potato brownie while walking around the quietly beautiful Boston neighborhood. The cute spot is super friendly – dogs are greeted at the door with a playful bowl of dog treats – and serves fresh and healthy café fare all day long.  The café serves seated dinner service beginning at 5:30 daily, and brunch on weekends.

Situated on the Freedom Trail one block from Faneuil Hall, Union Oyster House claims to be the nation’s oldest restaurant. Whether that’s true or not, the centuries-old tavern definitely has a history. Daniel Webster was reported to have drunk brandy and eaten plates of raw shellfish at the same oyster bar that stands today. The Kennedy clan has patronized the restaurant for years, and JFK’s favorite booth in the upstairs dining room is named in his honor. Although it’s not the chicest place to dine (especially given its location, in the center of the tourist attractions), Union Oyster merits a visit if you’re a fan of either history or oysters or a family looking for a lunch stop along the Freedom Trail. Those who want to sample the atmosphere without committing to a meal should split a half-dozen littlenecks at the bar downstairs and head elsewhere for dinner.