Torontonian in Boston
Always wanted to go, but never have had the chance. Really looking forward to seeing this city I've long admired from afar.
Looking for suggestions on authentic Italian, real Mom and Pop stuff. Remember, I'm from Hogtown; more Italians there than any other place on Earth outside Italy. I'll be spending a ton of time in the North End and would love some suggestions specific to that area.
Also looking for some serious Irish flavor, again, nothing chain or corny in it's forced "Oirish"-ness.
Lastly, some recs on where to get an excellent beer and I'm also interested in checking out some market and butchers shops and the like.
THANKS IN ADVANCE!
Toronto is so good for mom and pop italian that I'm not sure that's your best bet here. Here are some suggestions that TO (a great chow city, by theway) is not so strong for. Irish is a good idea and other hounds have posted. How about Portuguese. In TO, other the Chiado, which is very price, there isn;t much that i recall there. In Boston (especially Cambridge), there's a nice selection of inexpensive and delicious choices. O Cantinu, Casa Portugal, Sunset Grill and Atasca. Also, consider latin American or mexican. It's not a sgood here as elsewhere in the US but may be better than in TO. For example, Ricon Limeno in East Boston or Tacos Lupita (Mexican-Salvadorean)in Cambridge. Also, Boston is justly famous for ice cream and Christinas in Inman Square or Toscaninis near MIT are two. Unfortunately for most of these, you need a car or patience with public transportation.
Just in case you try to Google it, it's O Cantinho, not O Cantinu. Also, someone mentioned Formaggio Kitchen above -- when you asked for beer recommendations, you probably meant in a bar, but Formaggio has a selection of beers you might not find elsewhere and some of them are really good. My favorite is one that was aged in caves in upstate New York -- can't remember the name, but I've only seen it in Formaggio in Cambridge.
I live in the North End, and my personal favs are:
Taranta (very interesting Peruvian/Italian fusion; really good)
Modern Pastry for freshly prepared cannoli
Pizzeria Regina, of course!
As for Irish, James's Gate in Jamaica Plain has food that's very good, especially for a pub. It's easy to get to from the North End; just take the Orange Line from Haymarket Station to Forest Hills Station in Jamaica Plan. James's Gate is a 5 minute walk from there (5 McBride Street, just Mapquest or Google Map it). It'll give you a nice feel for a part of Boston the vast majority of tourists never experience.
Formaggio kitchen (http://www.formaggiokitchen.com/) in Cambridge or the South End
The Haymarket. Go Friday for shopping, Saturday for the atmosphere (perhaps the rudest market in the North East)
Not unique to Boston, but you might want to check out Trader Joe's since I don't think that's made it to Toronto (or even Buffalo).
If you are looking for Irish flavor (but not great food) I would recommend The Littlest Bar (if it's still open) and Mr Dooleys on Broad Street. The former is a tiny, charming, uniquie-to-Boston space and being the only non-Irish person there is always a possibility. Unfortunately, it's on the chopping block and it's days are numbered. If you go to the latter and Terry is tending the bar, then you'll probably get a chance to meet one of the most congenial bartenders in Boston. They have live music on the weekends that could border into McIrish, but some of it is quite good.
For more Irish-heavy bars, try The Irish Village in Brighton or Ned Kellys in Dorchester. Mind you, these aren't places to go here a sesiun, but frankly, not many younger people in Ireland do that anymore either, and they are in Irish ex-pat populated neighborhoods.
Be sure to search the board. We've had a zillion posts about the North End recently, and a good thread on Irish too. Matt Murphy's and the Druid are your best bets there, but not in downtown Boston. Are you willing to travel?
Kill two birds with one stone -- salumeria italiana in the North End is a great market. GREAT lamb and spicy eggplant panini across the street at Artu.