WJ, I''d suggest you pick up a copy of Bruce VanSant''s _Passages South_, which is the bible for the island-hopping-to-windward pathway to the E Caribbean from the USA''s east coast.
The prevailing winds (Trade Winds) are quite steady and swish back & forth like a cat''s tail, always oriented basically E''ly and much stronger in the winter. Periodically, fronts penetrate the islands, further south as Winter arrives and the lows are stronger, and so Option A is to ''stage'' in the E Bahamas until a front approaches (winds begin to veer, initially to the S) at which point the boat departs heading E, keeping up speed and making miles. The frontal winds veer NW, N and finally NE, aiding the boat''s progress E and SE. The wrinkles with Option A are that a) frontal winds don''t last more than 2-3 days (sometimes less), at which point the veer back to E and the boat is pushed S while beating into them, often ending up in the T&C or off the Silver Bank above the DR''s eastern end, b) the front the boat chooses may be too strong (and the crew & boat not well set up for it) or too weak (boat makes even less easting), and c) most crews (and often, their boats) don''t like going to weather as much as this routing requires. A sailboat''s motor can only do so much against the stiffened Winter trades.
Option B is the ''Thorny Path'', meaning its a prickly series of bumpy rides against wind, wind-driven current and swell, S & E while transiting down thru the Bahamas, T&C, the DR''s N coast and then sliding across the Mono to PR
''s S coast. The advantages are rest stops and the ability to choose weather for each leg, tho'' this requires good wx info & patience, both of which crews often lack.