I originally thought as you have, that it would make more sense to travel out of the Chesapeake bay
near Norfolk and then travel North. However, we really focused on the tides. They were with us for much of the trip. This made the north-south passage
SOG nearly equal to our speed through the water
. Giving us a significant advantage for both speed and physical distance traveled.
I would, however, like to try the route
as you suggest.