Have a look at a chart
smitty,
There's not much way to generalize, but if I were to do that, I'd say overall a N to NW is worst across the entire length of the span. I say that because there's nowhere from Fisherman's Island all the way to Chick's Beach which has less then, what, 12-15 miles open water between the span and the nearest land protection on a NW. North of approximately the First Island, the York opens up to the NW and right there you've got another, what, 15+ miles of open water a NW crosses before reaching the CBBT. A N comes dang near 200 miles from the mouth of the Susquehanna to the CBBT. What matters most is, as said before, "what direction, and for how long". NEs tend to be bad because they tend to remain in place for quite a while, even days, while a NW can be for a few hours to a day, day and a half following the passage of a cold front.
On the other end of the spectrum is a S to SW or SE. With that, much of the area parallel to the south shore of the Bay is protected and OK in 15-20 kt winds. I wouldn't hesitate to launch in Lynnhaven or Little Creek and fish out to, say, the Second in a S or SW 15-20kt. Probably wouldn't do the Third in that wind, though. Too much open water, especially on a SW, between land and the Third. Look at a chart and you'll see the area from roughly the Third on to Fisherman's Island is exposed to SE with no protection closer than West Africa.
The other thing to remember is to look at the "guesses" on a Marine forecast for the Lower Bay, like NOAA's "New Point Comfort to Cape Henry", as forecast winds are usually higher in those forecasts than those forecast for land. As often as the "guesses" are wrong for marine forecasts, trying to take a Norfolk, VB, Hampton, etc land forecast and translate it to the Bay is an exercise in futility.
Foy