Yes, it's a bit lawless. Buca di Beppo. 9 Historic Boston Restaurants for an Old-School Dining Experience The 7 Best Italian Restaurants in New York City's Little Italy Fior d'Italia opened in 1886 and claims to be America's oldest Italian restaurant it even reopened in a tent after the catastrophic 1906 San Francisco earthquake. "The Best Italian Sandwich!". The business experienced a major fire back in 2008 but has since rebuilt. Original fixtures and features are paired with whimsical touches, and the lights are low for a suitably debauched atmosphere. This Back Bay establishment (and sister restaurant to Mistral) is home to one of the citys priciest Italian menus. The real emphasis here is on ice cream, which is dressed up and transformed into tasty sundaes and floats. Fortunately, Coppa's wood-fired pizzas, robust pastas and small-plate bar snacks make it well worth the tight squeeze. Chiapparelli's Restaurant 4. Little Italy, Boston | Ultimate Foodie Guide | Cozymeal Chef-owner Douglass Williams of Mida. Amongst its menu of 30+ dishes, you'll see tempting and tasty seasonal options like goat cheese-stuffed zucchini flowers drizzled with lemon and honey, as well as a whole roasted fish that's artfully carved tableside. Carmelinas, open for a decade in Bostons North End, has a menu inspired by Sicilian fare, including quite a bit of seafood. 14 Best Italian Restaurants In Boston, MA 348 Congress St., Fort Point, Boston, 617-737-1234, sportelloboston.com. 17. Big bowls of pasta, rich sauces, fresh ingredients, ever-flowing winethere are many reasons diners cant get enough Italian food. Today the landmark still has its old-school charm. Situated between Central and Harvard Squares, this hip trattoria has aslightly retro feel thanks tothe amber glow of its globe lights and double-sided fireplace. First, it was the Copley Caf. Authentic Italian breads, cookies and pizza. [Photo: Facebook], Named from its original owner, Henry Marliave, a French immigrant from Paris, this restaurant opened its doors in 1885. 131 Brighton Ave., Allston, 617-254-9759, carloscucinaitaliana.com.