It means making a couple or three significant passages, but it's doable. Turks&Caicos to the
Dominican Republic; get a window for the Mona
Passage, then on east past
Puerto Rico into the British Virgins. From Virgin Gorda, to DesHaies,
Guadeloupe. From
Guadeloupe to Saint Lucia, then Saint Lucia on to
Grenada. This gives you plenty of bailout options, but if the
weather plays you would be able to do it in a couple of weeks.
We did this trip from
Georgetown,
Exumas in 2011, starting late April, arriving Grenada mid June, but we made more stops and lingered some (for fun and for weather). Quite a lot of motorsailing, but it is largely to windward for many of the 1000+ nauticals.