Re: U.S.-Bahamas, Crossing the Stream
The further south you set off for the Bahamas the better. Miami to West End is an easy sail. Jacksonville to West End much harder because you are heading into the Stream.
Do not be seduced by straight lines. The easiest route from Charleston, and we have done it several times is:
Outside from Charleston to Jacksonville then close to shore down the Florida coast where there is a counter-current going south. If the weather is bad just stay in the ICW
Personally I would go as far as Lauderdale, many would recommend Riviera Beach, so that I rode the Stream to West End.
Whatever you do you have to counter the minimum of 30-40 miles of northing that the Stream creates as you cross and it is much easier to make the corresponding southing on the Florida coast.
Going outside is really very benign and easier than the ICW providing you pick the right 2 day weather windows. If you jump off far north you will be out there long enough for a low to march off the coast and you are likely to be in some very nasty conditions.