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
(6 ft or less) and mast
vs. bridge (less than 65ft), are the biggest issues.