BRead in Boston
overall i find the quality of italian bread in bosston to be bizarre-pretty bad actually. The newcomers like Iggy's and Hi-rise made better breads.
DeAngelis Bakery- an old timer in East Boston basically makes white castle buns in the shape of italian bread. i also had very stale anisette biscotti there.
Hi-rise i found inconsistent overall, but had some tasty breads and cookies.
I am not sure if you are looking for bread in downtown Boston or if a ssection of the city, Roslindale, will do. I would like to recommend a small bakery by the name of Fornax. GREAT BREAD!! Although small some great varieties...garlic twist, olive bread, multi-grain, rosemary, romano batards, etc. If you get out to this area, give it a try. You won't be disappointed...
For challah and sweet sugar-cinnamon bread, try Cheryl Ann in Brookline near West Roxbury and JP