Mama Maria for dinner and Mike's Pastries for desert both in the North End.
USS Constituion (during the day) in Charlestown.
Walk across the Harvard Bridge and measure how many "smoots" you are.
Walk down Newbury St from Massachusetts Ave. to Arlington Ave and stop at the Boston Public Gardens and go visit the "Cheers Bar" (outside shot from the TV show) on the corner of Brimmer & Beacon Streets.
Your best bet is to use the commuter rail to get into to Boston and then switch over to the T to get around. Worst case scenario is you get stranded in Dorchester and have to mix it up with some southies....
Just remember, words with "-ar-" in them are pronounced like an -ah-
Another transplant in Tucson from Boston? I was the Fire Chief in Hingham for ten years before moving to Tucson.
Enjoy that two feet of snow they are getting. It might just interfer with a trip to Quincy Market and walking the Freedom Trail. Boston is a great city to see on foot, just not this time of year, or at least right now.
Boston is my favorite city to visit. Used to go regularly for work. My son is in Cambridge for school and we get up there at least once a year to see him now.
Don't try to drive right into town, especially during rush hour. Public transit is great.
The North End (T and walk). Cape Cod (Drive) . Lexington/Concord (Drive) and the Revolutionary War sites. Boston Common (T and walk), with Cheers right across the street. Not really worth going inside though. Mikes Pastries, L'Osteria for Italian food.
Legal Seafood is pretty good and there is a location north of Natick.
It's hard to even think because there is something interesting just about everywhere you turn. Study up so you don't miss the good stuff. Plymouth Rock isn't too far, but not much worth seeing IMO.