Glen, I think you will find Boston a very walkable city, and public trans right at your doorstep (Blue Line T station}. With that in mind it’s sometimes easyer to leave the rental in the garage.
As with any large city parking is at a premium and expensive. The roads here are confusing even to the locals, though many of the restaurants offer valet parking. No on to my selections.
Breakfast- I have to agree with Mandalay, Terrie’s in So. Boston is very good. I wanted to keep that one in my back pocket so to speak, but the secret is out.
Charlies sandwich shop in the So. End on Columbus Ave. is very good also.
For a Sunday brunch The Charles Hotel at Harvard Square, a bit pricey but outstanding.
Markets, Down the street 5min walk from your hotel is Haymarket it only runs on Fri. and Saturday mostly outside vendors but worth the stroll thru. You can get a fair to good slice of pizza there for $1.10 also our Italian neiborhood is right there.
For your evening dinning pleasure I’ll suggest a few with links
Not to be missed is Durgin Park right accross from you hotel at the Quincy market area. I’d do lunch there ask to be seated upstairs. wwwdurgin-park.com
An old Boston institution is http://www.locke-ober.com Fine dinning at it’s best with a strict dress code a great chef Lydia Shire
http://www.hamersleysbistro.com A very nice spot in the So. End of Boston. I don’t know how he dose it but the roast chicken there is tops. I heard from a waiter it’s the most requested item on the menu.
http://www.eastcoastgrill.net Damn decent, a mixed bag with seafood and good Q
This is in Cambridge so you may want to drive there about 15min.
Italian, My favorite and many fine choices. My spot of choice is Pagliuca’s on Parmenter St. in the No. End. I can and am very biased on Pag’s, it’s like an old pair of slippers just very comfortable, I’ve been going there for years.
There are many fine choices in the North End with most posting their menus outside for your convience. I’ll add to this as I think of them, I have some seafood spots north of Boston but your headed to Maine you will get your full there. Chow Jim