I usually went north of the islands, going west, as the wind is steadier and the seas more regular.
I like provisioning in SJ, and clearing into the US there as well, as long as you do not stop at any countries in between SJ and the US. The markets are well stocked and pretty cheap compared to StX. One can anchor for free, off the sport fishing club. If you do stop in SJ, a visit to “El Morro” is not to be missed!
Puerto Plata is a good emergency stop.
From there to Marathon or Key West, you have to navigate the "Old Bahama Channel". The Old Bahama Channel is at its narrowest between 22° and 23° North latitude, where it's rarely more than 12 miles wide and about 100 miles long. It can be heavily traveled at times and don't expect very many vessels in that area to have AIS.
After the Old Bahama Channel you will have to sail directly into the current, with the wind astern, to go West around the Keys. I've found it easier to cross the current and reach for Marathon, and the 7 mile bridge. North after the bridge are the "flats", the shallow water on the north side of the Keys. It's a fairly well marked channel, but not a good idea at night.
Once you enter the gulf, you can probably get good local knowledge.
