Re: BVI to Annapolis
My preference in that voyage is to sail toward the Northeast/Northwest Providence channel in the Bahamas, then through it and ride the stream north. On my last voyage in 2010, VI to Charleston direct, I was a bit too far east and we had no wind at all for the entire voyage.
By sailing just east of the Bahamas you can pick up a bit of "local affect" wind, which is caused by the shallows in the Bahamas heating up, creating a bit more breeze. However, this route does run one very close to if not over Silver Bank and quite near the T&C. This isn't so much a problem today, with GPS, but in the days of celestial navigation, it was of some concern.
Riding the stream around Hatteras can be a blast or a horror, depending on your luck, but again, today accurate weather forecasting is widely available, and there are plenty of places to wait out a northerly on the US coast.
"Any idiot can make a boat go; it takes a sailor to stop one." Spike Africa aboard the schooner Wanderer in Sausalito, Ca. 1964.