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Boston Drive to Southern Maine-July

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DH and I (late 40s/early 50s) have a few days (about 5) for a getaway while our kids are away at camp. We had looked at flying into Portland from DC area, but are having trouble getting on a flight for the days that we need (BTW - I have some flying "issues" - I don't do small commuter planes....the small-ish jets - are ok, though)
Anyway...now I'm thinking it would be easier to fly into Boston (many flight choices) and sort of head up to Portland, maybe stopping in a different town each night, and then heading back to Boston.
Good idea or not? Any suggestions for towns with things to do/see/etc between Boston and Portland? We've been to Ogunquit once a few years ago. Also - is getting (driving) out of Boston a nightmare?
Thanks for any help or suggestions!

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