West along the south coast of Dominican Rep?

[shantycrew]

We are about to sail our newly acquired Hardin Sea wolf fro Puerto Rico back to Luperon in the Dominican Republic. We plan to sail the south coast of both islands, harbor hopping as we go.
This will be a westerly voyage as far as Isle de Vache, then maybe Jamaica, southerly tip of Cuba, the Turks and Caicos and finally into Luperon on the north coast of the DR.

There seem to be quite a few posts on going west to east towards the BVI but precious little going the way we're planning.

Are we missing something, weird currents, winds etc or is it just a road less traveled.

We live in DR on the North coast and plan to keep "picaroon" there during the hurricane season and sail from there next November.

Any one done this or have any advice, thoughts suggestions.