If you’re looking for somewhere to chow in Boston, here are some of my favorite places.
In high school, my friends and I would race to the Porter Square location during our 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, but it’s the best quesadilla in town. Fact. Skip the burrito and get the crispy quesadilla. I recommend steak, al pastor, 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. Treat yourself to a couple of raw Littlenecks and a half order of fried clams too. You’ll be glad you did.
Cones bigger than your face redefine summer nights. Love me some soft serve or a Green Monster.
After some oysters at B&G around the corner, I’ll duck around the corner to Coppa for the best pizza in town. I always order the margherita pizza with blood sausage pepperoni. Small dishes and housemade pastas are dericious too. I’ll have what he [Jamie Bissonnette], is having.
Another BLGruppo entity of excellence. GM John Gertsen really knows how to take care of this chica. Can’t go wrong with his Sazerac.
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
Island Creek Oyster Bar (ICOB)
Oysters, oysters everywhere. Long bar and huge space in the heart of Kenmore Square. Must get the Island Creek oysters as well as Moonshoal, if they aren’t fresh out. Get the curry mussel app, BUBBLES (exceptional wine list, thanks to GM Tommy Schlesinger), and the infamous biscuit. Hands down the best biscuit ever.
For a special occasion or just a night on the town, take your honey for a tasting at Menton, where Top Chef and friend Kristen Kish is helming the kitchen. The service staff is knowledgeable, the food is comprehensive and the wine list is unrivaled in Boston. If they still have it, try the 2009 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.
I can never have too many oysters. Chef Michael Serpa knows just what I like: awesome wine list with bubbles, txakolí, and many French selections, east coast oysters, littlenecks, hamachi crudo and mussels in curry with cashews. Friends wanting more will opt for the Johnny cakes and the famed warm lobster roll. Lobster and butter–never better.
Want great sushi from a Japanese sushi chef, but don’t want to break the bank? For fresh and seasonal stuff, just ask 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. The Portland, ME native also has locations in Coolidge Corner and Comm. Ave near BU.
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 fixins: 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, specifically the Dorchester branch.
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.
