Sofra Bakery in Boston

Sofra Bakery (Photo by Kristin Teig Photography.)

Boston has always been a haven for history buffs, and it remains so: just take the Freedom Trail to see exactly where those irate revolutionaries threw an impromptu tea party back in 1773. It’s also the undisputed college mecca of the East Coast — puts the number of Boston-area college students at 250,000.

But in the past decade, Boston has also increasingly become a must-visit food town, complete with celebrity chefs, fascinating culinary tours and some really terrific new restaurants. It’s a fabulous food destination, filled with impeccably fresh seafood, glorious produce and quirky New England flavors and traditions.

Much like Chicago, Boston is a city of neighborhoods, each with very distinct characteristics. The South End — not to be confused with earthy “Southie” — has gentrified enough to populate with young families and millennials; the Fenway area is the bastion of Boston University students; the Seaport is touristy, while the North End is an extremely well-preserved Italian neighborhood, and Beacon Hill is very upper-crust. And like Chicago, there is useful and efficient public transport.

So, whether you’re headed to New England for a college visit, a family trip with baseball fanatics or just a romantic weekend getaway, you will definitely dine well in Beantown. As a bonus, it’s under a two-hour trip, with many direct flights running daily from both Midway and O’Hare.

Where to Eat:

Myers + Chang in Boston

Myers + Chang (Photo by Julie Chernoff.)

Both Myers + Chang (1145 Washington St., Boston, 617-542-5200) and Flour Bakery (with locations in Boston’s Back Bay, Ft. Point and South End neighborhoods as well as Cambridge) are owned by chef and cookbook author Joanne Chang, a Harvard grad who moved from management consulting to the world of food. Breakfast at Flour is a must for their unbelievable baked goods, egg sandwiches and coffee drinks, while Myers+Chang is the perfect spot for lunch (an easier reservation to score) or dinner. Their takes on Asian favorites (Szechuan Dan Dan Noodles, Thai Ginger Chicken Salad, Banh Mí with Braised Short Rib and Asian Pear, Wok-Roasted Mussels) and craft cocktails are inventive and palate-tingling.

Flour Bakery in Boston

Flour Bakery (Photo by Michael Harlan Turkel.)

Celebrity TV-chef sightings are fairly commonplace in Boston, especially if you dine at Ming Tsai’s Blue Dragon (324 A St., Boston, 617-338-8585) in Fort Point. This Asian gastropub has a tapas-style menu populated with signature Ming dishes. East meets West in creative dishes like Thai Chile Pimento Cheese with Lime-Spiced Tortilla Chips, Carolina BBQ Potstickers, Crispy Foie Gras Noodles and Duck Tostadas with Five-Spice Mole, all washed down with a Thai Basil Smash. Save room for the warm Deep-Dish Chocolate Chip Cookie with Ice Cream and Soy Caramel Sauce. No reservations accepted.

“Top Chef” alum Tiffani Faison has two restaurants in Boston’s Chestnut Hill: Sweet Cheeks (1381 Boylston St., Boston, 617-266-1300), a meat-and-three BBQ joint, and the recently opened Tiger Mama (1363 Boylston St., Boston, 617-425-MAMA), where she focuses on the fresh flavors of Southeast Asia, namely Thai and Vietnamese. Try her Coconut-Cured Salmon, Shrimp Saigon, Spicy Okra and deeply flavored curries and broths.

Menton in Boston

Menton (Photo by WEC Photography.)

Celebrated Boston chef Barbara Lynch has many restaurants in Boston, but it is the one-two punch of her five-diamond Menton (354 Congress St., Boston, 617-737-0099) and the more casual Sportello (348 Congress St., Boston, 617-737-1234) next door that really intrigues. For a true fine-dining experience, opt for the prix-fixe menu at Menton, complete with award-winning wine list and truly exquisite service. Sportello (which means “counter service” in Italian), though still on the pricey side, is the one I crave; trattoria favorites revisited, like the fresh, handmade pastas and tempting antipasti.

Sportello in Boston

Sportello (Photo by Brian Samuels Photography.)

Probably my favorite Italian in Boston right now is found in the South End at Coppa (253 Shawmut Ave., Boston, 617-391-0902), run by James Beard Award-winning chefs Ken Oringer and Jamie Bissonnette. It’s small, dark and intimate, but the food is full-flavored and loud. Stuzzichini (small bar snacks) like the Arancini di Zucca e Scamorza (risotto balls stuffed with squash and smoked cheese) and Chicken Liver Crostini really sing, as does the Burrata with blood oranges and smoked carrots. The toothsome pastas and blistered wood-burning oven pizzas are spot on.

If unique craft cocktails and killer poutine and burgers are more your speed, check out The Gallows (1395 Washington St., Boston, 617-425-0200) in the South End. Order a Ploughman’s Board — heavy on artisanal charcuterie and house-made pickles — and a veggie poutine to play nice with friends; if in a selfish meat mood, the Carpet Burger (with fried oyster, creole aioli and green apple slaw) is the play.

Oleana in Boston

Oleana (Photo by Kristin Teig Photography.)

In Cambridge, you must make a pilgrimage to Oleana (134 Hampshire St., Cambridge, 617-661-0505), the flagship restaurant of chef Ana Sortun’s mini-Mediterranean empire. She draws inspiration from Israeli, Turkish, Greek and Lebanese cuisines, and the flavor profile is exciting and a little exotic. You won’t miss a full bar with their very intriguing list of wine-based cocktails. Stop by her Sofra Bakery (1 Belmont St., Cambridge, 617-661-3161) for breakfast, a real highlight. Try the Spiced Barley & Lentils with egg, broccolini and garlic yogurt, or the spicy Shakshuka, a personal favorite. Biscuits are flavored with carrot and feta, or ginger and candied lemon; tahini runs rampant over the menu in a very happy way. Her newest hot spot, Sarma, is in nearby Somerville; I’m saving that for my next visit!

Sofra Bakery

Sofra Bakery (Photo by Kristin Teig Photography.)

In Harvard Square, Alden & Harlow (40 Brattle St., Cambridge, 617-864-2100) is an excellent option, located just down the block from the excellent American Repertory Theatre. Thinking of ordering their limited availability Secret Burger, among Boston’s best? You’ll want to pre-order one for the table, as they run out almost immediately. If you miss out, drown your sorrows in a cold New England craft beer and the Crispy Berkshire Pork Belly with grits.

We had a fabulous Sunday brunch at Puritan & Company in Inman Square (11666 Cambridge St., Cambridge, 617-615-6195). If you don’t get a pastry basket for the table (chocolate banana-nut bread, griddled cardamom pound cake, baklava cinnamon buns, Boston cream doughnut), you’re a fool. The Corned Beef Hash and the Spinach and Mushroom Quiche were phenomenal.

What to Do:

To really understand a city, you need to understand the food. Michele Topor’s Boston Food Tours are the way to go. Her North End Market Tour was a revelatory look at the history of Boston’s “Little Italy,” complete with visits to greengrocers, bakeries, salumerias, coffee and spice vendors, and a local liquor store with the most impressive collections of amari (Italian bitters) outside of Italy.

If you’re a baseball fan and have yet to pilgrimage to Fenway Park (4 Yawkey Way, Boston) and the “Green Monster,” maybe you’re not really a fan. The home of the Boston Red Sox, Fenway opened in 1912 and is one of the last remnants of old-school baseball. Babe Ruth, Ted Williams and Carl Yaztrezemski all played here.

Museums don’t come much more spectacular than the Isabella Stewart Gardner Museum (280 The Fenway, Boston), where the 2,500-piece collection is housed in Gardner’s old mansion, modeled after a 15th-century Venetian palazzo and built around a stunning, garden- and fountain-filled central courtyard. Behind the mansion is a 70,000-square-foot glass “addition” designed by famed Italian architect Renzo Piano.

Isabella Stewart Gardner Museum

Isabella Stewart Gardner Museum (Photo by Sean Dungan.)

Visits to local college campuses, such as MIT, Boston College, Harvard, Emerson and Boston University, are also a fascinating look at some truly astounding architecture, from red-brick colonials to metal and glass moderns.

Where to Stay:


Liberty Hotel

What do you do when you no longer need a prison? Turn it into a luxury hotel, of course. The once Charles Street Jail is now the Liberty Hotel, a Starwood property. The restaurant is called Clink; the cocktail bar — in the old drunk tank space — is the Alibi. There’s a lovely atrium space and a happening lobby (with the Liberty Bar), as well as Scampo, an Italian restaurant by Lydia Shire.

The Langham Boston

The luxury hotel group has taken over the old Federal Reserve building in the heart of Boston’s downtown. Luxury doesn’t come cheap, but the service and amenities are outstanding and the rooms are gorgeous with picturesque skyline views.

Nine Zero

Nine Zero in Boston

Photo courtesy of Nine Zero-Kimpton Hotels.

Located right on the Boston Common, you are steps away from American Revolutionary history … and the Boston Celtics. This Kimpton property sports one of Boston’s best hotel bars, The Highball Lounge, where breakfast is served each morning, and a party is happening Tuesday – Saturday nights.


Hotel Marlowe

Voted one of Conde Nast Traveler’s Top 25 New England Hotels, this property, also by Kimpton, overlooks the Charles River and provides easy access to Harvard, MIT and the Museum of Science. Striking room décor, hotel bikes for the borrowing, a yoga mat in every room, and a nightly wine reception combine to make this a super-cool place to stay.

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