Here is a recent thread in the FT Dining section under New England which you might find of interest:
http://www.flyertalk.com/dining/ftdi...ML/000006.html
In addition, do a search for "Boston" in the New England forum of FT Dining for more suggestions.
For an evening stroll you can: stroll around the North End for a true old Italian neighborhood; meander through the Freedom Trail; stroll through Cambridge. Those are just ideas which popped into my mind now.