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.