1. Are you nut Moron, stay home hahah.
2. Sail right into it this coming Monday nite and Tuesday Morning, the weather is likely to be wrong.
3. Hey, just perfect condition to wet my appetite, go for it.
I am ready, and fly out tomorrow nite to FLL.
In the first place you are missing a LOT of weather information looking at gribs. I've made this speech before so I'll shorten it - the GFS computer model that generates gribs smooths over barometric discountinuities like fronts. See my aggregation of synoptic charts here
Note that there is an occluded front stalled behind a mature low that dissipates over the weekend. That means thunderstorms in most cases. As the mature low dissipates the occluded front becomes a cold front and gets dragged along by the big low over the northeast which is likely to mean a significant wind shift completely glossed over in the gribs.
If you head offshore at 045T from FLL in SElys by midday on Friday, watch sea temperature to find the middle of the stream, the cold front will pass over you Sunday(ish) with the usual wind shifts. Really shouldn't be a problem on a big boat. Keep the boat moving and watch the radar. If the front moves fast or you are slow you may have to move East out of the Gulf Stream in anticipation of the wind shift - I don't like to give up the boost earlier than I have to.
As the high moves in behind the front you'll have light air for a while - all the more reason to be in the heart of the Gulf Stream.
Anything further out than that is guessing at this point. Watch the weather faxes.
I can understand to duck inside the port for northern wind, but not sure why Easterly will be a problem if one keeps enough sea room off the shoal.
Look at the Gulf Stream imagery. The curve of the US coast line drives the Stream along the coast of the Carolinas into a northeasterly direction before tipping further yet (driven by the Labrador Current among other things) and heading for Europe.
By the way, if you take the path espoused by others earlier in this thread and stay nearer shore watch for counter currents. You can really get knocked inshore. I'd go Gulf Stream center and out.