to Settlement point sounds like a trip that most likley will require you to motor
it's roughlly a 90 deg. course, which with the Stream, you will have to sail or motor
a 130 deg. course, to make 90 deg. over the bottom.
To sail you would need roughlly south to west winds. You never want to go with any northerly winds.
I would think it over, and while you are waiting for weather
, go down to Ft. Lauderdale and leave from there. it will be a much nicer trip. From ft. Laud. you could sail with south east winds. And the Stream would give you nice increase in speed over the bottom.
Light winds and engine
trouble, might land you in Bermuda!
Have a nice trip. And a safe one.