ASA and PSIA Instructor
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Re: Best week to sail in MA
The crowds in the Cape area are driven by the school summer vacation, when the schools get out the population in the Cape areas triples over night. So if you can pick and chose your time, I'd say go before the 4th week of June or after Labor Day.
As with other posters, I'd recommend the after Labor Day choice as the weather and water temperature are still summer, and places like Cuttyhunk, VH, or gasp! Nantucket, which would be elbow-to-elbow the week before, are pretty much empty.
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