My favorite restaurant in the Boston area is Craigie on Main (James Beard award), which has an outstanding tasting menu. Great cocktails and an interesting wine list. They also happen to serve one of the most famous burgers in American (cover of Bon Appetit), but they only make 18 a day, so you need to be there at 5:30PM sharp in the bar to snag one. Personally, I think their tasting menu is much better than Troquet or L’Espalier. L’Espalier is certainly a sexy experience, but I find it a bit tired. Bistro du Midi also has a good tasting menu, although I can never go back there again for an embarasing reason I won’t mention lol.
If you want a pure tasting menu experience, check out The Tasting Counter, which was Boston’s highest rated restaurant on the Opionated About Dining Top 100+ list last year. It’s dropped to #117 this year behind Barbara Lynch’s Menton at #110. It’s trying to be Boston’s Brooklyn Fare or The Catbird Seat, although I don’t think it is remotely in their league. But a very fun experience (although the wine pairings are all natural wines and not that great imho).
If you want a great wine list, Troquet has one of the best you’ll ever see, with great prices, and the food is very good too. Just did a 5-course tasting menu there a couple of weeks ago (they also have a 7-course). Unfortunately, you’ll be too late for the Summer Wine Sale, which ends Labor Day Weekend. We had a pristine bottle of '86 Ch Margaux on Monday for $150 ($998 on their list). Wine steal of the year!
As mentioned, Erbaluce is great, although he doesn’t use dairy or butter, so it is non-traditional. Best carbonara I’ve evah had! I also love Pammy’s for Italian (fairly new). But personally, I wouldn’t take 2 teenagers to either of these. Haven’t been to Giulia. SRV would also be a great choice for Italian (Venetian).
Surprised no one mentioned Oleana, which is probably Boston’s best restaurant (James Beard award). Although many people prefer their sister, Sarma, which I’ve never been too.
Boston’s best cocktails are at ArtScience, although I haven’t been since they switched chefs (the photos on Instagram look amazing).
If you like sushi, the omakase at Cafe Sushi in Harvard Square is as good as a 1 Michelin Star in NYC (the omakase, not the whole restaurant, which is very casual, although newly remodeled). Get reservations for the counter and you might sit next to Christopher Kimball! I would much prefer to eat there than O Ya, although the latter is an amazing experience.
The original Row 34 is actually the one in Boston, not Portsmouth. Their sister restaurant, Island Creek Oyster Bar is legendary (these are the oysters Thomas Keller serves at Per Se and French Laundry), but I personally think Row 34 is much better. Skip the famous Neptune Oyster in the North End (Italian district), my last meal there was very weak and it’s a pain in the ass to get into anyway. For great seafood near Neptune, go for North Square Oyster next to Paul Revere’s House. I prefer their lobster roll anyway (both hot and cold versions). Select Oyster Bar is also very good, although expensive.
Not knowing your teenager, I don’t know where to suggest. If they like seafood, I’m sure they’ll be happy at Row 34. Our best pizza is probably Area Four near MIT, where Obama visited. Asian, you might try Tiger Mama (Tiffany Faison from Top Chef). World Championship winning BBQ at The Smoke Shop near MIT (also locations in Seaport and Assembly Square, although I prefer the original). Tiffany Faison’s Sweet Cheeks is also supposed to be good BBQ, although I haven’t been there. Kirkland Tap & Trotter is the more casual sibling of Craigie on Main. I bet they’d like Myers + Chang, a nationally famous Asian fusion restaurant.
Here’s Boston Magazine’s current Top 50 list, which is a reasonable list of our best places: