One thing to think about with respect to your routing is that if you are planning on going on down the
Carribean chain it will be an upwind slog / bash from the eastern
Bahamas all the way to
Puerto Rico / USVI /BVI. You will be tacking into the trades all the way. You might want to get some experienced crew to help you go direct, Norfolk to the "Isalands", and do the
Bahamas on the way back. Just a thought. As far as the ditch is concerned,
depth vs
draft (6 ft or less) and
mast vs. bridge (less than 65ft), are the biggest issues.