My father ran charters out of USVI in the late 70's-until Hugo came through. I can remember him making one point perfectly clear. When headed to the BVI, clear in at the first/closest port of entry, regardless of your final destination or they will make your life a living hell if they catch you. Seems more than one boat was seized and chained back in the day, and your US lawyers are pretty much useless within the BVI legal system. They can bleed you dry $$$ wise while you try to sort it out.