I just made that jump and basically singled the whole way. Catch the back end of a northern and it is a cake walk (but dont get caught between the low and thie high as I did on one leg!).
Not interested in crewing, just wanted to give you very recent, first had advice. It is a very easy hop. I do not know if that would ease your skippers mind about it. If not, tell him that it is going to be in the 80's all weekend in SW FLorida!!! I can post pics if you want of trip south and what you get when you get here!!!!
PS What marina are you at? I stayed at Pan City Municipal Marina. Nice folks. I just left a couple of weeks ago so wonder if we might have crossed paths?
PSS Get a sleeping bag for the run south for the onwatch night crew (and maybe the day crew). We saw below freezing north of Tampa.