The off-shore weather has now changed: the Bermuda
high has broken down and the fall lows are starting to march through. While there are tropical waves off the Caribbean
that could turn into tropical systems.
You can work south now down the ICW and close inshore until you get to Georgia
. In a small boat, I used to do it in a Corsair
F31 which was fast but hardly robust, the further south the easier the crossing to the Bahamas
to West End rides the Stream and takes, in favorable winds out of the south or west, 20-24 hours even in a small boat. It is much easier to push south on the US side where there are multiple safe havens.
Then it is a matter of waiting for a window that will give you favorable wind
across the Gulf Stream
without the danger
of a strong northerly low or a late tropical storm. Unless you are expert in weather it might be worth subscribing to Chris Parker's weather prediction service