Have not done the trip all the way from Cuba since I'm US citizen and visiting Cuba is discouraged. I have made the trip from the south coast of Haiti
to the Virgin Islands
so similar route
I did best staying close to the south coast of the islands which blocked the worst of the winter
trades which were very strong from the NE when I made the trip. We did see some land/sea breeze effects but the winds were pretty light and we motored most of the trip.
I would check latest security
issues before stopping on the south coast of Hispaniola. I hear Ile a Vache may be OK. Not sure about DR. Western PR I think is OK, the VI just fine. Then you're almost there.