From several months of studying that region's
weather, at this time of year I think you would like to leave right after a cold front comes through, which will give you nice stiff N-quadrant winds, of course there is some chop that comes with them but with a nice reach and not too far from shore you should be fine. Otherwise you will generally face SW prevailing winds, the last thing you want given that you also have to avoid a NE gulfstream
current. pete