Re: Best week to sail in MA
The weekend after any holiday is usually the best time to go anywhere (sailing, skiing, etc) if you don't like crowds. The holiday weekends are the best if you do like crowds and to be part of all the action. It seems like most people here don't like crowds.
So it depends on what you want. If you don't like crowded anchorages, mooring fields and restaurants then the Sept and Oct advice is good. However, I also find that the week before labor day is usually pretty good as most of the kids are back at school or home getting ready for school and the week is fairly mellow in comparison to the rest of July and Aug. You get all the summer weather benefits and if you can extend your cruise to include Labor Day, you get an extra day.
If you are looking for some action, go 4th of July. If you can't go on the 4th and still want action, skip the week following the fourth and go anytime after up until the week before labor day.