@sailingsoon. Where are you planning to depart from?
Here in the Stuart area the settled weather wind is normally SE. This is probably the weather you want for the crossing. That pattern can last days - plenty of time to cross. Interrupting that settled weather are the Northers which bring Northerly winds and sometimes high winds. After a Norther (Which is a cold front), the wind will shift to NW, then NE for a day or two, then E, and finally SE again. The Northers are largely a Winter/Spring phenomenon. The cycle is 3 - 5 days depending on how strong it is.
There is always the risk of thunderstorms which in many cases are not frontal in origin. They can be violent. We have had very little rain in the past 3 months - maybe longer. So very little T-Storm activity (Here). That is due to change pretty soon as the wet season begins.
I haven't been here long enough to conclude this, but I think the wet season comes in as SW winds become more prevalent due to the higher dew points on the Gulf side of Florida and as temperatures increase. I have noted that the weather forecasters challenge then is to guess what time the T-Storm will be as opposed to whether there will be one or not.
If you have the app Storm try putting the location to Stuart and scroll to the bottom where the temps, and wind are shown in a graphical format. It becomes easy to see the pattern.
I hope this helps. These are only my observations since moving to Jensen Beach.
The unasked question is: sailing or motoring? If motoring you just have to wait for favorable weather and go, remembering to allow for the set of the Gulf Stream. Sailing, you have several choices, all poor. You can tack dead to windward in our prevailing east wind. Or you can start out as far southwest as Islamorada and remain on the starboard tack. This substantially lengthens the trip. Or you can wait for the wind to turn northwest after a cold front. But that wind will clock through north and northeast before returning to east. So timing is critical. As Diochner pointed out, north winds make the Gulf Stream really unpleasant.
While wind vs. current can sometimes create a bumpy ride, there are so many eddies in the Gulf Stream as to make this consideration moot. The Gulf Stream isn't a homogeneous flow or direction which is why we largely ignore it when doing that trip. The flow can change direction within a mile or less sometimes which is why weather and wind direction and speed should be the primary considerations.