Family Style Red Sauce - North End - 20 people
I was looking around Quincy Market, but I think it's easier to try the North End.
Need a casual family style red sauce italian where a group of 20-25 parents and 14 year olds can chowdown on good bread, baked clams, chopped salad, pasta, chcken parm, shrimp oreganata, veal, etc etc. Standard Stuff.
Good food - attire will be shorts. Not looking for anything formal, austere or stuffy, but also not looking for a dive or anything real cheap.
I was thinking mother anna's, but it appears it's not family style and even tho we'd order a ton of food, they frown on bigger platters for groups.
Based on the experience you are looking for, you may want to try Vinny Testa's in the Back Bay. Just hop on the green line a few stops to Copley and walk 3 blocks.
They serve everything either as single plate or family platters. It's not the most amazing Italian food ever, but they'll take reservations, their food is pretty tasty, they have the room (unlike the North End), and they focus on large family dinning.
I love the North End but the best place for you is Magiano's in the Park Plaza area. It is always family style there, the food is good, the artmosphere not stuffy at all and you won't be dissappointed. If not there then I would go for L'Osteria in the North End and see what they can do for you.
I think Mother Anna's would actually be a good option for you. It's fairly big, casual, and inexpensive, and the food is excellent.
Other options might be Antico Forno on Salem Street (though it's pretty small) and Cantina Italiana on Hanover Street. Ricardo's has a lot of room, but it's probably not the type of place to go in t shirts and shorts.
Saraceno's, La Summa, and Massimino's might also be good options.
I'd strongly suggest avoiding La Famiglia Giorgio, La Famiglia Spagnuolo, Joe Tecce's, Piccolo Venezia, and Dolce Vita, all of which might also seem like possibilities. Bad food, bad service, and tourist-trap snags are all very likely at these spots.