North End Food Tour (Self Guided), Boston

Nestled at the crossroads of Hanover and Cross streets, offering stunning views over the city, the park, and all the action of Boston’s North End, including a wealth of Italian restaurants, Mother Anna's is the oldest family-owned eatery in the area – a true testament to its enduring appeal. In business since 1932, it manifests four generations (!!) of fine Italian cooking and, over decades, has seen many a restaurant come and go in the neighborhood – from single digits, back in the early days, to nearly a hundred these days.

Mother Anna's remarkable longevity, surviving even the disappearance of the old Central Artery that once divided the North End, speaks volumes about its enduring charm and culinary prowess. Attesting to this is a loyal cadre of "regulars" who frequent the establishment weekly. The delicious food keeps people coming back for more, in large part thanks to the recipes kept in the family and passed down through generations – from Anna Travaglione, the founder, to John Caparella, Anna's grandson and current owner who runs this place alongside his three sons. At Mother Anna's you can enjoy Italian cuisine at affordable prices, complete with plenty of wine and drink options. Don't miss the perennial favorites: 'Gnocchi Liliana' and 'Shrimp Exquisito'.

Today, Mother Anna's serves as a gateway to the historic North End. On a hot summer day, their famous patio, filled with umbrellas, offers respite from the sun, and when night falls, patrons are treated to a breathtaking view of the Boston skyline.

Tucked away in the tiny Board Alley, just off Hanover Street in Boston's North End, you'll discover two beloved establishments collectively known to locals as Bricco Alley. The first of these two shops is Bricco Salumeria & Pasta Shop, renowned for its exceptional made-to-order sandwiches, widely regarded as some of the finest in the city. Meanwhile, its neighbor, Bricco Panetteria, operates as a full-service bakery producing the highest quality bread, earning accolades such as "Best of Boston" in 2014.

The bakery is a brainchild of Frank DePasquale, owner of a chain of restaurants, who opened it specifically to provide bread for his chain. The bread is handmade and made fresh daily. Additionally, the bakery offers a nod to the Sundays of DePasquale's youth by preparing hand-made pasta just like his mother did back in Italy. This delectable pasta perfectly complements the high-caliber Italian products available at Salumeria next door, many of which are imported directly from the "old country" and include cheeses (notably mozzarella and focaccia), meats, olive oils, vinegars, and tomatoes—everything you require for an authentic Italian feast, at your fingertips!

Outside, a small area with a few tables invites you to savor your culinary delights while being enveloped in the aroma of freshly baked bread all the way. As passersby stroll along, they often find it nearly impossible to resist the temptation and stop by to pick up a loaf or two for themselves. Succumbing to this delightful trap is not only recommended but also ensures a cherished memory of your time in the North End. You might even find yourself making a habit of returning periodically to relive the experience!

Modern Pastry is like the pastry king of the North End, and it's got a die-hard fanbase. Even though this family-owned bakery has been around for ages, it's got a cool and modern vibe—hence the name. These guys are famous for their mouthwatering pastries, including old-world cakes, fancy cupcakes, cookies, pizelles, and chocolates. But the real star of the show, the reason you might have to wait in line...?

Well, people here are serious about cannoli, and there's a bit of a showdown between Modern Pastry and another big-shot bakery, Mike's Pastry, for the title of "Cannoli King" in Boston. Tourists usually flock to Mike's, but the locals swear by Modern. You've gotta taste both to pick your side on this tasty turf war. And while you're at it, head over to Modern Underground for a nice cocktail to go with your dessert.

Modern's indoor seating area is much like a social club where the owners pride themselves on knowing their regulars by name. Whereas cookies are the main highlight — sold by the bulk for as little as $5 per bagload (what a deal!), they also serve breakfast and brunch before noon. So if you're in the vicinity struck with veracious appetite, be sure to pop in and, after finishing your meal, treat yourself to, say, some delightfully flaky 'sfogliatella' (a lobster tail pastry) and a coffee.

The family of chefs running this bakery has been perfecting their pastry skills for over 150 years, across different parts of the world, so they really know their stuff.

Tip:
When lines get long, they open a smaller shop next door that sells the same stuff as the big bakery. Only the locals are in on this secret.

Set on the North End's Hanover Street, in the very heart of Italian quarter, you'll find Caffe Vittoria, proudly claiming to be Boston's first Italian cafe since way back in 1929. And you know what? That claim actually holds up because this place exudes an old-world, funky, retro charm that'll transport you to rustic Italian towns and give those New England Starbucks a run for their money.

Small, metal-rimmed chairs and tables scattered about across the four floors of well-worn marble with three bars, glass display cabinets, and a treasure trove of vintage coffee machines and espresso makers, not to mention the prints, are good enough a reason to visit here, at least once, and is as close as it gets to a museum dedicated to the evolution of the modern cup of espresso.

Speaking of coffee, and especially the cappuccino, it is well worth your time, and will deliciously pair with the various Italian pastries they serve. Word on the street is that many celebrities and politicians swing by this North End hotspot for some of the best hot chocolate, cappuccino, and cannoli in Boston, maybe even in the whole U.S. of A!

Here's the kicker: all the bars at Caffe Vittoria serve up liquor, including some Italian Grappa that's definitely worth a shot... or two. And if you're feeling extra fancy, head to the basement where, back in 1995, the owners opened a cigar bar called Stanza dei Sigari – the last surviving smoking lounge in the city. The service is always outstanding, and the ambiance makes it a great place to kick back and relax.

You can't miss Mike's Pastry in Boston's North End – it's one of the iconic pastry shops that draws hordes of tourists to the neighborhood. Always buzzing with activity, this place is best known for their cannoli (especially the Florentine cannoli), those tube-shaped, crispy pastry shells fried to perfection and loaded with sweet, creamy goodness. And let's just say they aren't stingy on the portion size!

Alongside the famous cannolis they also offer a variety of other large pastries (emphasis on large!). So if you're not so much into cannoli yourself, worry not as you can't go wrong with any of the biscotti, cookies, lobster tails, cream puffs, or macaroons at Mike's.

Still, if you're indeed a cannoli fan, be sure to stop by Mike's after dinner for one (or a few) of their 19 cannoli flavors, including plain, Nutella, Oreo, Limoncello, and others. Fun date night idea: grab the cannoli package and make your own at home. Greedy!!!

Mamma Maria is a top-tier restaurant in North Square, known as the oldest public square in the United States, once frequented by pivotal figures in American history. Perched atop a small hill in a 19th-century brownstone, this place has the magical ability to transport you straight to "la Patria" with its old-world charm, attention to detail, and an unsurpassed warm welcome. If you're a fan of waiters in neckties, an elegant white tablecloth atmosphere, and an European period setting, Mamma Maria is tailor-made for you!

While it boasts the distinction of being the sole Italian restaurant in Boston to earn Four Diamonds from AAA and garner a recommendation from The New York Times, Mamma Maria doesn't aim to be the most avant-garde. Instead, it steadfastly adheres to the classics, offering a seasonally-inspired menu with an emphasis on time-honored Tuscan dishes with an elegant twist. Although the menu changes daily, the restaurant is particularly renowned for its Osso Buco (veal) and Rabbit Pappardelle.

Another distinguishing feature is the striking view of downtown Boston – a dramatic contrast between the city's skyline panorama and the winding streets and cobblestones of North Square, all visible through the expansive floor-to-ceiling windows found in the five multi-level dining rooms. This, combined with the rich, hearty recipes honed over decades, is what truly elevates the eatery.

If you're planning your visit strategically, enjoy a meal here before a snowstorm, and you'll have the perfect excuse to hibernate for a few cozy days afterward!

If you're looking to ditch the lines altogether and have a genuine Italian grandma-style experience, be sure to swing by Bova's. Hidden away on Salem Street, this tiny family-owned bakery has been serving up delights since 1932. What sets it apart? Well, it's open 24/7, and in a city that tends to hit the hay early, it's your go-to spot in the North End when those late-night sweet cravings strike.

Now, if you're keen on cannolis, you're in for a treat because they come in a variety of flavors here, so feel free to fill up a to-go box with assorted cookies and pastries right from the giant glass display cases up front. That said, the crunchy, Florentine cannoli and those huge, flaky lobster tails are among the best reasons to visit the North End no matter the hour. Keep in mind, though, that Bova's is a classic bakery where things aren't always perfectly uniform, unlike the pastries you'll find at Modern or Mike's.

Renowned for its wide range of goodies, from various breads to pastries, cookies, tarts, cakes, and pies, the place also caters to those craving something more substantial, like fresh-baked calzones, subs, spuckies or Sicilian-style pizza. This place is the real deal, and it's a cash-only operation. It might be a little cramped inside, so you'll probably want to take your treats outside to enjoy.

This cute little shop might initially appear to be a café, but it's not – it's a true-blue store. While you can indeed find coffee here, it's strictly in bean form, as they don't brew it on the spot. The air is rich with the aromatic embrace of coffee, and that alone is reason enough to step inside. And once you do, prepare to be transported back in time, surrounded by brass weighing scales, a vintage mechanical cash register, and an impressive array of glass jars brimming with coffee beans. You'll also discover a treasure trove of seeds, nuts, candies, along with an assortment of spices, herbs, extracts, and olive oils imported from Italy, all offered at great prices.

This little slice of nostalgia has been a neighborhood fixture since its establishment in 1932 by Anthony Polcari, an Italian immigrant. It's like a living museum, a place where you can soak in the old-world charm and savor a taste of Boston's Italian heritage. One of the ex-employees, who had worked here for 26 years, now runs the place and is dedicated to preserving the Polcari family legacy alive. The fact that you'll often find local food enthusiasts and coffee connoisseurs frequenting this place is a testament to its authenticity.

The staff here are not just friendly but also more than happy to share their knowledge about coffee and regale you with tales of North End history. If you're ever in doubt about what souvenir to bring back from your Boston adventures, simply grab a pound of Polcari's coffee. And if you happen to visit during the summer, don't leave without trying their homemade Italian slush – a delightful concoction of shaved ice with a splash of lemon. It's an absolute must on your North End exploration checklist!

Billed as "The Most Authentic Italian Restaurant", Antico Forno makes it tough to argue with that claim. Spacious enough to handle a weeknight impulse visit, family in tow, this mainstay in Boston's North End manages a cozy mom-and-pop atmosphere with the world-class traditional cuisine. Entrees like 'Saltimbocca di Pollo' and 'Linguine al Frutti di Mare' hearken back to the old country, but Antico Forno is best known for its pizzas piled high with house-made Italian sausages and mozzarella. "No gimmicks, no kitsch", just traditional thin-crusted Neapolitan pizzas from a wood-fired brick oven that are absolutely divine and really distinguish this North End stalwart.

Still, Antico Forno is much more than just pizzas; it's all about Southern Italian cuisine done right – fresh and bursting with flavor. From hearty pasta dishes like linguine baked in parchment with tomato sauce and a generous helping of shellfish to other "spot-on" Southern Italian specialties, this place offers a casual and relaxed setting that'll warm your heart and satisfy even the heartiest appetite. Plus, it's proof that dining in the North End doesn't have to mean squeezing into tight quarters.

Beyond the scrumptious food at reasonable prices, Antico Forno has a full bar and even a private dining room. This spot is quite popular, so be sure to book ahead and secure your spot for a taste of Italy right in Boston.

How far would you travel for a lobster roll? If you're unsure, make a pilgrimage to Boston's Neptune Oyster and discover the answer. This North End oyster bar is undeniably one of the city's most famous eateries, despite its laundry list of less-than-ideal attributes: the long lines, snug quarters, lively hubbub, slow service, throngs of tourists, and a menu that can take a toll on your wallet. But all that combined is overshadowed by one indisputable fact: this place serves up seriously amazing food!

Established in 2004, Neptune Oyster is a shining example of East Coast raw bar perfection. The simple, subway-tiled interior gleams with retro charm. While many patrons flock to the raw bar, those who opt for substantial fare indulge in one of the city's most renowned lobster rolls, available hot with butter or cold with mayo. Other standouts include juicy burgers topped with crispy fried oysters and composed entrees like a whole Rockport mackerel prepared Veracruz-style. Given the cramped environs, be ready for a wait that often stretches out the door as you vie for one of the marble-topped tables or a spot at the bar. But once you're here, you'll know without a doubt that it was worth every moment!