Is Speciald the name of your boat?
It will keep my eyes open for your boats this winter. I am currently in Toronto but the boat is in Mobjack Bay. We are returning to the boat on Sunday and can leave any day from Monday onward. If the weather is not cooperating we might move closer to the entrance to Chesapeake Bay to leave from.
It is interesting looking at the 96 hr (and longer) weather forecasts to try to get a sense of when we can go. There is a remarkable low over southern Hudson's Bay on the 96 (
Atlantic Briefing Package) with a central pressure of 966 mb. Lets see, that is Saturday morning. Give it a day or so to move eastward (including the stationary front across the southeastern US) and it might be a go for Monday or Tuesday.
Our plans for the winter are pretty fluid. I think we are going to spent a couple of weeks in the USVI and BVI and then head to the Grenadines for a time and then slowly work northward in the spring.