There's no one answer to this question, right? I mean, you could sail directly to Freeport from Beaufort with a northerly...
Under ordinary conditions, i.e., the conditions you will find 7 out of any 10 days, I would suggest that anywhere north of Lake Worth
(West Palm) is likely to force you to tack your way back to Freeport. To be honest, if I was planning to sail to Freeport I would plan on leaving from Port Everglades (Ft Lauderdale). You can do the math on the gulfstream pretty easily, call it an average current
of 2.5kt, wall-to-wall, heading almost directly N in that region. Vector in a prevailing E-SE wind
and you'll see the problem. Like I said, it is POSSIBLE from anywhere, but the likelihood is higher the further south you get.
Of course, motoring or motorsailing change the landscape dramatically, I'm referring to sailing across.