I absolutely agree with Jthaw. We tried it about 8 years ago. The "plan" was to sail from Provo (T&C) to Fajardo, PR. It took about 3 days of beating ourselves and the boat before we got smart enough to turn back to the Turks and Caicos
. Then, later, we did the Thorny Passage
. Although Van Sant makes a lot of good arguments and has a lot of great advice, that trip is also something of a bitch! You might also think about Frank Virgintino's route, through the Windward Passage and then along the south coast of the DR. I've never done it but there is some sense to it.
As Jthaw implies...once you get below 30 degrees north, you are in the trades. They will blow at 20-30 kt out of the east almost all of the time. So, no matter the route, you are going to be working and working to get east. The offshore route (sometimes called route 66) makes a lot of sense if you don't have an overwhelming desire to see the southern Bahamas and the Turks and Caicos
. If you do: It would almost
be worth returning north and going offshore.