Eventide in Portland has been mentioned a few times in this thread. And for good reason, it was fantastic. We were a group of 6 and most everyone was in agreement that they liked it more than Neptune in Boston.
Holy Donuts in Portland was really good.
We only stopped in Portsmouth to eat dinner but what little we saw (at night) I would have wanted to go check it out again We ate at a place called Cure and 2 folks in our group thought that was the best meal they had on our trip.
In Boston, Freedom Trail is a must and I would follow it all the way over the bridge to Bunker Hill monument and USS Constitution. Our other meals in Boston, unfortunately, were not well-planned so I can’t be much help with restaurants other than I did really like Neptune
Thats about all I’ve got. we were there during the marathon this year and weather was brutal. Still got to Fenway which was awesome (it snowed, which was way preferable to the rain).