We flew to Boston and did Vermont, New Hampshire, drove up White Mountain, did Acadia, then down the coast back to Boston in 10 days. It was fun. It was about 16 years ago. Take it as it presents itself and enjoy.

2200 miles. It was a blast. No agenda.

We spent most of our time in Maine. The people there are really great. The coast can get really crowded though especially around Acadia. But it's damn sure worth it.

Have a great time. You won't regret this trip.

There is a lot to discuss, some great food, some things to see and places to stay.
To see on a drive like that
North shore Aging port cities, Salem, Gloucester, the Northern Essex Museum, the which museum, the house of 7 gables, Walden pond, the beauty of Rockport or Marblehead and the little clam and lobster shacks associated
South shore aging port cities
New Bedford, Fall River old school whaling ports and Battleship Cove.

Boston is beautiful and historic but like many mid size cities. The old north church, Daniel hall, the freedom trail, old Ironsides, the tea party ship

There is not much NH Coast, it is only about 10 miles long and they just had terrible flooding in Hampton and Rye. The Lakes are the things to see in NH.

Oh my, so much

I'd go out to the end of the Red Line and rent a car there for the rest of the trip.
I love Boston because it is so compact and walkable.
Don't miss Italian food in the North End!!!

Gloucester, Google the menus of seafood restaurants and look for one that has fried Cod cheeks.

Maine, Bob's seafood shack, Rt 1, Kittery. If you get to Acadia and the sky is clear, take an evening ride to the top. Bring binoculars if ya have 'em. Miley Way is visible. If it is closed in evenings, ask locals or cops where to go that is not crowded.