Tim, Your best bet is
head north from DR to
Turks and Caicos, to the
Bahamas, then jump off from Cat Cay to Key Biscayne, then south down Hawks Channel. Otherwise you are heading dead into
wind, seas and currents. You might try hugging the north coast of
Cuba and trying to find the counter
current until south of
Key West but you run the risk of the USCG seizing your
boat if you enter into Cuban Waters. That is if you are American Flagged.