If you’re looking for somewhere to chow in Boston, here are some of my favorite places. They’re all over the map, in more ways than one:
In high school, my friends and I would race to the Porter Square location during our 35 minute lunch breaks. Now Anna’s has 6 locations throughout Boston: Porter Square, Davis Square, Coolidge Corner, Harvard Ave. MIT, and MGH. I’m not claiming this is authentic Mexican food. It’s just the best quesadilla in town. Skip the burrito and get the crispy quesadilla. I recommend getting the steak, carnitas or lengua quesadillas with salsa, guacamole, lettuce, hot sauce and jalapeños. Oh and wash it down with a fresh squeezed key-limeade 
At one point I frequented B&G at least once a week, downing about a dozen [east coast] oysters paired with bubbles (Simonet Cremant de Bourgogne). The fried clams, fries and Littleneck clams are worth it too. Oyster aficionado? Chat it up with super knowledgeable oyster guru, Jen the GM.
The guys behind Journeyman opened this bar, hidden just through the wall of Journeyman and in the same back alley of Union Square. It’s your unassuming, neighborhood place to catch up with friends over a drink or three, if bar manager Sam Treadway is in the house. They offer a bar menu and some items from Journeyman. These guys always make me feel at home.
Hands down the best burger in the world. I’m open to trying other burger joints, but for now Bartley’s reigns supreme. So juicy. Always packed with regulars, tourists and Harvard students. Bring cash. Leave indecision at home.
Huge bang for your buck in a cone or a cup, or both. This is where we would spend our summer nights [because there's nothing better to do in the 'burbs]. Green Monster = Yum.
After some oysters at B&G around the corner, I’ll walk over to Coppa for the best pizza in town. I always order the margherita pizza with blood sausage pepperoni. I also check out of they have any new offal offerings because I love tripe, sweetbreads and all that goodness + Jamie Bissonnette.
My ultimate go-to for stellar cocktails and chill ambience. Some of my favorites include: 1919, Sazerac, The Old Cuban, French 75 and a darn good Manhattan. Indecisive? Just chat with the bartenders and they’ll whip you up a custom concoction with your choice of alcohol and accompanying flavors. Count yourself golden if you’ve arrived just in time for a glass of their punch. I can never get enough of John Gertsen and the Barbara Lynch Gruppo!
Felipe’s offers similar “Mexican” fare as Anna’s, but I always prefer Felipe’s to Anna’s, especially if I’m in the Harvard area. For some reason, it just tastes better to me. Perhaps less greasy? You can’t go wrong with a steak or carnitas quesadilla here. With jalapeños and guac, of course
Cocktail bars in Boston are the new black. The bar is managed by the ICOB (see below) crew and they do it right. If Scott is working the bar, you’re in luck. Can’t go wrong with a Manhattan. Check out their ice shaping machine. Spherical ice? Hai. kudasai.
Island Creek Oyster Bar (ICOB)
Hip ambience, long bar and huge space for larger parties if that’s what you’re looking for. Here you’ll find super fresh oysters, some of the best french fries in town and great fried clams. Stick to the east coast varietals, namely Island Creek, Onset, Wellfleet. I’ve never gone wrong with ones from the Cape and Rhode Island. If you’re the entrée ordering type, try the lobster roe noodles. Oyster sliders? Make it three, please.
Tucked away in a back alley of Union Square, Journeyman has what Boston lacks–thoughtfully and meticulously prepared, each dish comes out when it’s ready. No heat lamps, no unnecessary sprinkling of chopped parsley, no pretence. Open kitchen fare. The menu changes frequently and you have the option of 3, 5 or 7 course prix-fixes. My first experience there, I loved the Asian influence in their simple veggie dishes. Kudos to a restaurant that has figured out how to make veggies appetizing! This kind of intimate, locally-sourced dining is trendy in Paris now (i.e. Le Chateaubriand, Spring, Frenchie to name a few)…I hope it catches on in Boston!
This gastropub-esque watering hole in Cambridge has quite the selection of artisanal beers on tap. Their hoppy selections are great and I love that they always have something from Victory Brewing Co. Excellent stuff. Parking is tricky but it’s totally worth it. They also dish up a delicious brunch as well. Try the pork belly hash or cuban sandwich. For a late-night snack, order a cone of fries or a plate of fried calamari with shishito peppers.
The aspiring ‘Per Se’ of Boston. For a special occasion or just a night on the town, take your honey for a tasting at Menton, where the service is knowledgeable, the food is comprehensive and the wine list is unrivaled in Boston. If they still have it, try the Cassis from Domaine de Bagnol. Don’t leave without touring the pristine kitchen and if you’re a chef, check out their Molteni. Remember to save room for their [exotiquely flavored] mini-macarons.
Want great sushi but don’t want to break the bank? For fresh and seasonal stuff, just ask the Japanese chef Masaki-san. Better yet, just get his omakase. If uni is in season, you’re in luck. He gets the fresh urchins from Maine, so fresh they’re still in their spiny shells. If hirame (fluke) is in season, get it. Chances are he went fishing yesterday.
Don’t miss this tiny shop in the hustle and bustle of Harvard Square. Arguably my favorite slice in town, Otto’s does pizza justice. Crisp crust, creative toppings (if that’s what you dig, they’re known to serve over 30 different kinds…but I’m a pepperoni girl through and through). Generous slices. Sprinkle with chili flakes. You’re set. I also hear they’re opening a larger (60 seats) spot in Coolidge Corner this Spring. Woo!
Innovative, modern Japanese food with international flavors that pique your palate on multiple levels at various points throughout the meal. O Ya takes modern Japanese food to new heights. I hope you don’t have allergies or preconceived notions. Flavor progression is everything. Here’s my 15 course omakase [in very specific order]: Kumamoto oyster with watermelon pearls, Hamachi with viet mignonette, Otoro with lotsa wasabi, Shima-aji and uni with ceviche vinaigrette, Hamachi with spicy banana pepper mousse, homemade potato chip with truffle aioli, Santa Barbara sea urchin with valencia orange, Amaebi with uni (if it’s in season), Chutoro with republic of Georgia sauce, Warm eel with thai basil, fried Kumamoto oyster with squid ink bubbles, Sashimi of shiitake and chanterelle mushrooms, Squid-ink soba, Onsen egg, Seared petit strip loin with potato confit (ask for no truffle oil), Foie gras with balsamic chocolate kabayaki and sip of aged sake. Order a bottle of Yuki No Bosha sake. Skip dessert. Wicked detailed, I know, I used to work there.
With two locations in Dorchester and Chinatown, this franchise is as good as it gets when you’re craving a steaming hot bowl of pho on a wintry night. I get mine with all the fixes: tripe, tendon, eye round, shank…oh and don’t forget the sriracha! Unless you have a Vietnamese grandma or a frequent flyer pass to Vietnam for the real deal, your best bet is to hit up Pho Hoa. Hope they remember to leave out the MSG!
Neopolitan pizza from this venerable, hole-in-the-wall establishment. I love the crunchy, airy crust and the simple joy of their pepperoni pizza [with a flurry of red pepper flakes]. It’s been in the same hidden nook forever. Let’s keep it that way.
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