My experience is similar to Todd's. Heading south from the Chesapeake, at this time of year or later, is a pretty iffy proposition weatherwise. It can go either way -- quickly. Last time I sailed from Annapolis to Tortola we left in mid-November. Trip down the bay to Norfolk was pretty nice and not too cold. We then headed SE on a diagonal to cross the Gulf Stream. We got pounded by rainy and cold weather, and some pretty big waves, for the next 8 days. It was no fun. I suggest leaving earlier.