I agree with others above, save Maine for a year or two. You could get there quick pretty quick in a smoky sou'wester, but getting back home in the same conditions could take forever. Also, Maine (being a lee shore in the summer southwesterlies over cold water) is much more fog-prone in August than is southern New England.
I like the Boston Harbor islands and Cape Ann idea that SailingDog suggested . While the latter might be crowded, the former might not be.
That said, I made it from Marblehead to Boothbay, and back, in a week once, on a medium-speed 30-footer. But it was a stretch, and I was much younger then. All the way from Buzzard's bay, no way.
Whatever you decide, enjoy it. But keep your distance estimates realistic, and the "admiral" will be happier. And therefore so will you..;-)