I do most of my fishing in Buzzards Bay and Vineyard Sound. Now I know that BB is very rough (towards the Cape) when there is any kind of wind from the West, especially SW. Vineyard Sound is very rough with SE winds. I understand the principle, but I just want to make sure, if I were to fish out off of Chatham, a West wind would be ideal correct? Anything form the East would be pretty bad right?

Thanks. I just want to be sure I am on the right track before trailoring my boat all the way down there.

Anything over 10-15kts out of the East off Chatham will get unpleasant. You also need to figure in the swell if fishing inshore or rips. Several days of East wind (or a passing offshore storm) can generate impressive waves. Put the tide against it and you want something more than a trailerable boat under you. Then there is fog :).