We've done several Beringer Bowls (overnight from Marblehead to P-town), and to add others have said - prevailing winds tend to favor heading south and then cutting east across - at least at night. Last year for Labor Day weekend, we just did a straight shot, and it was a wild ride. Winds from the southwest, but swells from a low-pressure system out in the Atlantic left us with huge swells running at right angles to the wind-driven waves. And this was on a 26-ton full-keeled cruiser! Just pick a good weather window and you should be fine. And make sure the VHF is in good working order!
We'll probably see you around Salem Harbor - we'll be in Hawthorne Cove this summer. Look for the pirate ship!
1979 Formosa 51 Ketch
Homeport: Marblehead, MA USA