Re: Best week to sail in MA
June is beautiful, but a bit of a crap shoot. Shore temps are great, but ocean water is still cool, so it will be chilly while sailing offshore. Whether places like CuttyHunk are open and in full swing will depend a bit on how stormy and warm the spring has been. Even then, only on weekends.
The week after Jul 4th will be the easiest to get moorings and slips or find an anchorage in the height of the summer. Once you get to Aug, you do start to risk hurricanes. We had to quick haul the weekend before Labor Day a couple of years back. Even if they don't threaten land, they can kick up some nasty coastal seas. Not every year.
The week after Labor Day is also great. Crowds die down dramatically but everything remains open.
Keep an eye peeled for regattas and/or festivals, where all bets are off. Newport is nuts year round. I've suggested to many to go to Connanicut, across East Passage, and take their ferry back and forth to Newport. However, some like being in the action. Countless places to go of all kinds from quiet to mobbed.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.