95 is definitely the way to go as far as a direct route up the coast towards Maine.
As far as seeing things in Boston, your best bet is to park your car at one of the T stops (Boston's subway system) outside the city and ride the T all day to see everything in Boston you want. To travel in and around Boston with no experience with Mass-hole driving habits and the Big Dig your whole family will be miserable. Trust me! It's tough enough being from the area and trying to get around. Stay away from the Orange line as much as possible
As far as the T stops, Government Center (on the Blue line) will let you out at the top of Faneuil Hall with all the shops, food and street performers. Plus you can take a tour on the Freedom Trail or a Duck Tour of the area there. You can take the Red line T to Park St. to see the Boston Common with Frog Pond for skating and ice sculptures that are being made for First Night (New Year's) festivities (they'll probably still be there). You can take the Red line to Downtown Crossing for all the shopping (if you're into that sort of thing.) Fenway Park is off the Green line at the Kenmore stop, just walk up Brookline Ave when you get off. The North End is where you want to be for dinner if you're in Boston, be sure to stop at Mike's Pastries for dessert, the Cheesecake is insane!
North of Boston, you can travel through Gloucester and Rockport along the coast until NH. Portsmouth is a great town to see with tons of interesting places, then you'll go through Kittery in ME where all the outlet stores are. Or if you want to see more country sights and aren't in as rush, the White Mountains are incredible especially around the Laconia and Conway areas. I'm sure there's other stuff like that in ME but I don't know enough to recommend any.
Just be ready for nasty weather when you get up here, we've had 17 in of snow this month already and MA pretty much came to a screeching halt last Thursday because of it. It took my sis-in-law 8.5 hours to drive home from work 50 minutes away because non-essential employees were all let out at the peak of the storm and the plows couldn't get through. I hope you have a 4X4!
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