I just saw this and I have to say what a fine fine post Dave has put in here.....totally expected of course!!!I would add too, for your friend's interest, if not perhaps use, that it was more common to sail to the island destinations and then back to the mainland when going south rather than north. Again the factors affecting this were the gulfstream current and the prevailing winds, not to be ignored in days when square rigs were still in some use.
Great post again Dave.
Spaw