Going "as far South as possible" is not a good
route choice to the islands. I suggest not leaving the coast much further South than Charleston. The further South you go before going off-shore, the more you will have to beat to windward to get to PR. With a 55'
mast, I assume that your
boat is 35-40 feet long. Should be big enough for the off-shore
work.
Secondly, do not wait until too late in the season as the North-easters will start. I've done the trip to
Puerto Rico after Thanksgiving and had good
weather all the way but the frequecy of fronts increases as you get later in the season. If you havn't done the trip before, consider joining a rally. The
Caribbean 1500 starts November third out of both Hampton and Charleston.
Thirdly, I hate the ICW. You can only make 60 miles a day at best and after a few days you will feel like your eyes are going to pop out of your
head. At 2 meters draft, count on running aground more than a few times. If you are
sold on the ICW, go inside between Norfolk and
Beaufort, the ouside to Wilmington, inside to Cape Fear, then outside to Charleton or Fernadina.