Re: Thorny Path
Going south of Cuba is not really any easier, you have to get through the Yucatan Straits which if part of the Gulf Stream and flows 2-3 knots to the north. You need to be in Cuban waters to avoid the current.
Going through the Windward passage and then east might be a little easier than going north of Hispaniola but I have not done this route.
We were in Cozumel and decided it was easier to ride the trades than bash to windward and sailed north to Miami and then east out to 67W which appears to be the harder way but was so benign we only broke $9 of equipment...one shackle.
The shortest route is not necessarily the easiest when going into wind and tide.