Partly the reason I asked is I'm curious who might be interested in a drag-race from Sarasota to Key West. Its approx 170 nm so it would be better to start the race right as the wind shifts to the NW after a frontal system moves through. That might mean starting in a good bit of breeze.
It's going to be tough to get sailors that are capable of scheduling a run like that (and resources) around the weather!
