We never plan more than a few hours in advance anymore. Way too much hassle and disappointment with any plan made by one person for a large group.

If Anegada or even North Sound is on the wish list? We head that direction as far as we can go on the first good weather window when the crew is up for moving the boat. From Anegada or North Sound we work our way downhill when the mood striked the entire crew. If it is flat calm? Then I will likely move the boat to North Sound or Anegada before most the crew wakes up on the first morning. We no longer grow crashing upwind on vacation. The great news about the VI there is always someplace to go downwind. Or you can just stay where you are another day. There are no bad places in the BVI/VI.