Well...if you want an offshore passage then the only way to go is East/NE first...then south. If not...then the "Thorny Path" through the Bahamas, Dom Republic, and
PR is the route which limits passages to 24 hours or less on each leg. A great book on making this cruise "thornless" is "A Gentleman''s Guide to Passages South" by Bruce VanSant.
Once you are down in Florida..you have 700 miles of easterly bashing into strong trade winds to get to the VI...so the "thornless" passage is the only practical alternative.
Hope this helps...GB