Young married couple arriving in Boston on a Wed. in late May and spending 2 days there at the beginning of our trip. We have never been to Boston, so what should we do, where should we stay? We would like to see some of the history, but also enjoy some good resteraunts, and a neat irish bar or two. We will rent a car in Boston. Where should I pick up the car if from Boston, we will drive up to Kennebunk, Maine, where we will be spending 3 days with friends. We then head off to Albany, NY to make another friend visit. We will drive back to Boston on a Tuesday. Our plane does not leave until Thursday. Should we spend these in Boston or is there a cool place to spend a day or two between Albany and Boston? Any suggestions are appreciated on special places or activities.

The Berkshires are just a bit east of Albany and the MA Pike makes them convenient for getting back to Boston as well. The favored town seems to be Stockbridge, but Lenox is nice as well. It'd be wise to look into reservations in advance as the area has a heavy draw from NYC and vicinity.

Check out Sturbridge Village if you like history. Otherwise, go on to Cape Cod for one of the extra days.

On your way from Albany to Boston, you could easily visit southern Vermont and the Berkshires. Take Route 7 east from the Albany area into Bennington, Vermont. Bennington is a nice small city--you could walk around Old Bennington, go to the top of the Bennington Battle Monument, and go see Robert Frost's grave to name a few things. If you're into Outlet shopping, from Bennington, drive north on Route 7 to Manchester. If you love outlets, you'll love Manchester. After visting Manchester/Bennington, you could head south on Route 7 to the Berkshires (Lenox, MA area) and spend another day. From Lenox, Boston is a quick 2 hour drive down I-90. I see you're coming in late May--if you're going to be travelling on Memorial Day weekend and will need hotel reservations, make them ASAP! Hope this helps!

Look at quikbook.com for hotels. I stayed at the Copley Plaza, which is gorgeous, for $160/night. May might be a little more expensive, but the service has good prices.
Eat at Legal Seafoods (there are several) because it's a local favorite as well as tourist place - some great fresh fish.
Depending on when the snow melts (you don't want mud season), consider stopping at the Windham Hill Inn in Southern vermont (windham, vermont). they have a website, and it's spectacular.
Also, the Mayflower inn in Northwestern Connecticut, is beautiful. And you might see a celebrity.
If you want to take the ferry to Martha's vineyard and stay over one night, book the Charlotte Inn in Edgartown.
All these places are expensive but worth it.