Our teenagers can't agree on a summer trip. One wants to see a new city with history. Son wants mountains or beaches. It seems like Boston with a trip up to Portland and over to the White Mountains would give us all that plus good seafood. However, I've never been to that area.

Thinking about two days each in Boston, drive up to the mountains (maybe Mt. Lafayette area), and then over to Portland, Maine area and get a VRBO in one of the coastal towns with a beach. It seems like only a 2.5 - 3 hr trip between each location.

Thoughts from anyone who has spent time up there? Are there any must see spots in those areas?

If you're going to Portland, I'd go on up to Acadia NP.

In the process of planning this exact trip for this coming August.
Loose route as follows:
3 days Boston
1 day Stopover in Portland
3 days Acadia
2 days White Mountain area
*Concord/Lexington stop on the loop back to Boston

Did a similar trip last fall to check out the foliage. Flew into Boston and went straight to Portland.
Then 2 days in the White Mountains and 2 more days in Stowe, VT. Didn't spend any time in Boston but did the whole trip in 8 days.

I think your trip is very doable.

Very doable but keep in mind once you get off I-95 or I-93, it can take a while to get around. Even I-95 at least can be pretty terrible with traffic if you time it wrong, north from Boston on a Friday or heading south out of Maine on a Sunday afternoon

It is only 60-80 miles on the map from White Mountains to Portland for example but can take longer then that on the little winding roads. Same for heading up Rt 1 along the Maine coast once off the interstate. A lot of traffic on two lane roads. You can sit in traffic like you might in Houston or Dallas in Conway, NH and Wiscasset, Maine if you are unlucky on timing. But, gorgeous part of the world.

And if you love to eat, stay a little longer in Portland then you might think. Incredible food scene, of course great seafood but do not limit your self to just lobster rolls. All kinds of great restaurants that incorporate local seafood. It is a just great little city all the way around.

Did something similar last year going through Boston to Portland and up to Acadia, then across to White Mountains. I-95 is of the devil, my God so much traffic and so many wrecks. Once you get into Maine it's not as bad, but still not great. Driving through Maine and New Hampshire backroads will give you some amazing sights, but it is slower than what most of us are used to.

I'm currently planning our vacation for this year and we're going back to Portland and Acadia, but leaving out White Mountains this year. It was just too much, we could easily spend a week at both, and I didn't account for the extended travel times. So we're just focusing on Portland, Camden, and Bar Harbor this go around.