We've done the Pillsbury Sound passage every month of the year, except December. We've had no problems, even on small boats with crew that got a bit green on the way to Anegada. There are swells in Pillsbury Sound, but they are long period and short lived. Spring/summer is a non-issue.

I would sail with CYOA, add two more days to your itinerary or fly into EIS.

Cheers, RickG