fwiw my 2c..
Given your vessel is ICW
friendly my suggestion would be to set off in early/mid october from cape>block Island>Norfolk, then ICW
to Morehead city
NC. Stage in NC for a window then off from there... the gulf stream
is relatively close, and relatively narrow from there..take advantage of the SW winds to go ESE/SE until you start to pick the trades..then kinda due south to the USVI
This has sizeable merits vs a direct offshore
a) you chase the warm weather
south before the winter weather
b) you are always within striking distance of somewhere reasonably safe in the event of a late season storm..
c) you are tackling the stream only needing a solid 24hr window/forecast
d) its the shortest leg of long passage