Packed with fresh seafood, historic sites, cute townhouses, great cocktails, and outstanding chefs, Boston's not a half bad town to spend your Valentine's day in. Here are our recommendations for where to eat in the Greater Boston area.
The High End Blowout: Craigie On Main
Tony Maw's Craigie on Main in Cambridge is consistently one of the best, most exciting restaurants in the city. They offer a 5-course $149 menu for Valentine's day, in both meaty (think: Red Miso-Marinated Axis Venison) and pescatarian (Butter-Poached Spanish Turbot) versions. It's where I proposed to my wife, and yep, she said yes. That's a pretty good track record for success.
Runner Up: No. 9 Park
For Fancy Food on a Budget: Lumière
For great food at more wallet-friendly prices, head out to the suburbs and hit Michael Leviton's Lumière. The 3-course Valentine's day prix fixe gets you dry-aged rib steaks and oysters, sweet potato gnocchi, and Champagne sorbet, among other dishes, for $75. Tack on another $30 for the wine tasting.
Cozy Neighborhood Spot: Bondir
Chef Jason Bond has a high end cooking pedigree, but he's a country boy at heart, which makes for a restaurant with the cozy feel of a country home—fireplace and all—with the attention to ingredients and technique you'd expect out of the fanciest white tablecloth restaurants in the city. The menu changes daily, but expect a mix of winter vegetables (e.g. Winter Beet Salad with beets cooked three ways in a pistachio vinaigrette), handmade pasta (Spelt Flour Spaghetti with fresh Perigord truffles and Guinea hog prosciutto).
If You Can Get In: Coppa Enoteca
Ken Oringer and Jamie Bissonnette's first-and-a-half venture (Bissonnette was the chef at Oringer's South End Tapas restaurant Toro) has been a tough table to score since opening three years ago, but if you can get in, you'll have fun spliiting small plates of Italian bar snacks (Beef Heart Crostini or Sea Urchin Panino), house- or artisan-made salumi, very decent wood-fired pizzas (try the bone marrow, horseradish, and beef heart pastrami pie), along with pasta and larger format plates.
Runner Up: Toro
For Seafood Lovers: Island Creek Oyster Bar
These days, it's nearly impossible to enter an oyster bar on the East Coast without seeing Island Creek oysters, farmed in Duxbury, MA on the menu. But the eponymous restaurant in Kenmore Square is arguably the best place to enjoy them (along with over a dozen other oyster options on an average night). You'll also find excellent versions of New England classics like lobster rolls, fried clams, fish & chips, and apple cider doughnuts.
Runner Up: B&G Oysters
For Sushi Lovers: Oishii Sushi
I would have recommended that you make the trek out to Chestnut Hill to eat at the (usually) exquisite Oishii Sushi bar. But now, with a gorgeously decorated, full-service restaurant in the South End, you don't have to. The sushi and sashimi are the real draw here, but their salads (try the Kaffir Lime Duck Salad), soups (with homemade tofu skin!), and appetizers (Berkshire pork gyoza and grilled hamachi collar) are faultless as well.
Runner Up: Uni
For Chocoholics: L.A. Burdick Chocholates
What started as a small chocolatier in Walpole, New Hampshire, has built a mini empire off of its excellent hot chocolate and cute chocolate mice, with two locations in Boston and one in New York. Their other confections—cakes, truffles, cigars, and the like, ain't half bad either.
For Romantics: Lala Rokh
I had my first-ever Valentine's day date at this great Middle Eastern restaurant in a townhouse decorated with exquisite Persian art. The atmosphere is so cozy and romantic you'll feel like a private guest at a bed & breakfast. If that doesn't win your date over, then the lazy post-dinner walk towards the Boston Common down quaint Charles Street in the warm afterglow of braised lamb and pomegranate seed surely will.
For Southern Ex-Pats: Hungry Mother
Full-on Southern hospitality in Yankee territory. Food & Wine's 2009 Best New Chef Barry Maiden's Hungry Mother slings classics like skillet cornbread, catfish courtbouillon, and fried oysters in a classed-up, romantic-yet-casual setting. Pro-tip: Do not leave without trying the angel biscuits.
For Vinophiles: Belly Wine Bar
Central Bottle on Mass. Ave. has quickly become the go-to spot for wine buyers in Cambridge. The same crew recently opened Belly Wine Bar & Charcuterie in 1 Kendall Square, in the space next to the Blue Room (also run by the same team). Its walk-in only menu of house-made charcuterie and small bites is perfect if you want to focus on their well-curated wine selection (and who wouldn't?), but if you want a bigger blowout, make a reservation for their fondue for 2. (If you're part of the anti-valentine's day crew, their arm + a leg dinner, will feed a party of 4 to 12 on every part of the pig imagineable.
For Cocktail Lovers: The Hawthorne
Jackson Cannon, the bar manager you came to know and love from Eastern Standard up and got himself his own joint next door and called it The Hawthorne. Decked out with comfortable armchairs, carpets, and living room furniture, you'll feel like you're having cocktails in your uncle's house. If your uncle had good taste, was rich, and knew how to mix a drink better than almost anyone in the city, that is.
Runner Up: Brick and Mortar