Looks like the seas and the wind on the nose is no go. I like the the idea to head to the straights of florida and around that way from Isla. What do you think about heading from Isla to west coast of florida and jumping the ICW and cut across inland. My rig is 56' and should clear.
I'm not sure of gunkholing along the southern coast of Cuba, Hispanola, PR
would be all that good. I would probably end up motoring all the way.