Re: Best week to sail in MA
I envy you the decision. Just moved away from MA but had some of our best fun down among the islands. Your first choice is likely to be whether you swing East or West. Unlikely you can do Nantucket AND Newport (agree that Connanicut is a really good alternative to the latter) in a week unless you want to be sailing really hard core all the time.
The week after Labor Day is great but, depending on whether you prefer having the place to yourself or a bit more "atmosphere", you may not want to rule out either of the last two weeks of August. You may have to book a couple of moorings but you have plenty of advance notice as long as you are not too ambitious about how big a hop to make in any one day so that if the wind totally dies, you can motor.