Boston is associated with a lot of history — and that includes culinary history — from chowder and Boston cream pie to the Fenway frank and fish and chips. But the city has long had its own culture around Italian cuisine, dating back almost a century in some instances. Say “ciao!” to the 20 best Italian restaurants in Boston on Caviar, based on what Caviar diners order most. Andiamo!
Picco is a pizzeria that happens to make some of the best ice cream in town. Along with their sorbets, they’re all made and frozen in-house with locally sourced milk and housemade toppings. Bonus: They don’t use high-fructose corn syrup or artificial colors or flavors. Choose a pint from an array of flavors — and don’t forget the chocolate sauce.
James Beard Award nominee for Outstanding Chef, Douglass Williams is the visionary behind this Italian trattoria in the South End. Also a Food & Wine Best New Chef, Williams opened MIDA in 2016; its name means “he gives me.” Thus, every meal is meant to be a gift just for you. The bucatini all’amatriciana and the eggplant Parmesan always win a place in our carts.
Posto’s Italian wood-burning oven allows the pizzaiolos to cook pizza at temperatures in excess of 850 degrees. Posto imports the finest 00 pizzeria flour and most flavorful San Marzano tomatoes from Italy, and they use their own fiore di latte mozzarella cheese. This Somerville spot also serves antipasti, pastas, and salad, and they have a very respectable selection of wine and craft cocktails.
4. Bar Mezzana
Savor the simplicity and beauty of coastal Italian cooking at this South End gem from culinary industry power couple Colin and Heather Lynch. Named one of the Best Restaurants for Pasta in Boston by Boston Magazine, Bar Mezzana is here to satisfy your carb cravings in an elegant manner with dishes like goat cheese and ricotta ravioli. Do not resist the urge to splurge on the paccheri pasta with lobster. You won’t regret it.
They’ve been making pizza at this Boston mainstay for nearly 100 years, so it’s fair to say they know a thing or two about the art and craft of pizzamaking. One of the most iconic restaurants in Boston, Santarpio’s is one of our go-tos for a pie. The Works, with mushrooms, onions, peppers, garlic, sausage, pepperoni, anchovies, and extra cheese, always finds its way into our cart. (Don’t worry; you can skip the anchovies if that’s not your thing).
Time Out named this Beacon Hill establishment one of the 21 Best Italian Restaurants in Boston in 2021, so you know you’re in good hands with whatever you order from Grotto. The fare here is hearty and satisfying, with selections like gnocchi with short rib and gorgonzola, and classic spaghetti and meatballs that would impress any Italian nonna. Slip a slice of the warm chocolate cake into your cart for the perfect finish to your meal.
North End fixture Giacomo’s doesn’t accept cash or reservations — which is fine because you don’t need either to enjoy their Italian American cuisine with Caviar. The portions are big, and the prices are surprisingly low here, with popular dishes like lobster ravioli and chicken Marsala ringing in at under $26. We always start off with the fried mozzarella because we can’t not order fried mozzarella.
What started out as a sandwich shop in 1992 has evolved into a North End favorite serving a greatest-hits menu of all the dishes you think of when you’re in the mood for Italian (which is always for us, btw). Fried calamari and charcuterie plates are among the starters, and there are salads and pizza, like the Fico with fig, prosciutto, gorgonzola, and mascarpone, plus pastas, Parms, and a killer tiramisu.
Did you ever have a sandwich that was so good that it basically ruined you for all other sandwiches? Then it must have been from Monica’s. There’s a sub for every appetite, but we encourage first-timers to order the Italian sub with prosciutto, mortadella, salami, provolone, lettuce, tomato, onion, oil, balsamic, hots, and pickles. You’ll never look at a sando the same way again.
10. Tony & Elaine’s
This is a self-proclaimed red-sauce joint. The food feels old school in the best possible way, as if they’ve been open since the days of the Rat Pack (or at least the Brat Pack). But this North End spot has only been open since 2018. This is the place you can indulge your unabashed love of mozzarella sticks, garlic bread, and eggplant Parmesan. Order a pint of their marinara to make your home into your own red-sauce joint.
You’ll find seasonal, Mediterranean-inspired fare at this Central Square restaurant. For almost eight years, they have been crafting classic dishes with modern twists, like the duck croquettes with guanciale aioli, cured egg yolk, and charred leek, and the shaved Brussels sprouts salad with crunchy quinoa, red pepper, blue cheese, and a Dijon vinaigrette. Take the cannoli — straight into your cart.
12. Bar 'Cino
The name of this Brookline spot is inspired by the Italian word for neighbor (vicino) and when you receive your order, you’ll feel like your cool chef-neighbor just dropped off a casual spread made to share. Build a veritable buffet for you and your crew; the antipasti plate is a delicious way to get started. Add a salad, like the Tuscan kale, followed by a grilled pizza. We strongly recommend the roasted mushroom pie.
Tartufo is an award-winning Italian restaurant featuring authentic Abruzzese and Mediterranean cuisine. Opened in 2004 in Newton Centre, Tartufo is renowned for its unique dishes, like the minestrone Abruzzese soup and shrimp al cognac. The chicken Parmigiana and the limoncello mascarpone cake get us every time. Every time.
For nearly a decade, Locale has been drawing pizza lovers to the North End. There are standout starters like baked ricotta and eggplant rollatini to kick off your meal. Twelve pies on the menu are dressed to impress, like the pistachio pesto with homemade pistachio pesto, pork sausage, and mozzarella. But, with all due respect, our fave is the Silvio, with mozzarella, cherry tomatoes, prosciutto, burrata, and pesto.
Since 1936, this Medford deli has stayed true to its authentic Italian deli ways. They’re all about ingredients here, so you’ll find things like imported aged prosciutto di Parma in many dishes. Along with the many pasta and entrée offerings that Bob’s offers, this is another spot for a stellar sub. The Classic 50/50 features half chicken Parm and half meatballs for people who just can’t decide between the two.
Quattro is an award-winning Italian rotisserie that serves a dozen brick-oven pizzas made with authentic Italian ingredients, like imported soppressata and mozzarella di bufala. Get one — or two! — but don’t overlook the signature half rotisserie chicken with mashed potatoes and au jus. If you’re looking for something more substantial, we suggest the steak pizzaolo, a thin-sliced rib eye with garlic, oregano, red wine, and colino tomatoes.
17. Strega Italiano
At Strega Italiano, they believe in food with heart, made with love from recipes handed down from generations past. It’s all about homemade pastas, secret-recipe sauces, and house-baked desserts at this Back Bay hot spot. You’re going to want to go in for four courses here. May we suggest the grilled octopus followed by mushroom agnolotti and a New York strip? Chase it with the signature torta cioccolato. Prego.
Feast on a bountiful array of Italian specialties at Benevento’s in the North End. Opened in 2010, Benevento’s is your one-stop shop for everything you love about this cuisine. From more than a dozen pastas and 10 pizzas (we love the Spukonie, with sweet Italian sausage, ricotta cheese, tomato sauce, mozzarella cheese, and fresh basil) to entrées like sausage cacciatore, they deliver a meal to remember.
We can never get enough pasta. If you feel the same, Basta Pasta in Cambridge is for you. Spoiler alert: Even though they serve 17 kinds, they aren’t just about pasta. You’ll also find thin-crust gourmet pizza, salads, burgers, paninis, and salads. Still, the chicken ziti with broccoli always has a place in our hearts — and our carts.