I did the trip in 1998 and passed east of the Bahamas (because I had already done the Berrys and Exumas) via north side of Turks and Caicos, San Salvador, Eleuthra and then through the Abacos (did most of them), then on to St Augustine (There is a customs/immigration issue). I liked it because it gave me a direct deep water route with easy access to island stops when I wanted. Going west would have committed me to either shallow water and winding routes or the congested east Florida coastline.
I considered straight from Grenada to St Croix, then Puerto Rico and west of Bahamas to Florida, But sailing straight up the island chain leaves you the opportunity to stop almost every night in a protected anchorage in the leeward of almost any island. This is strictly the no stress way to do it. If you''re in a hurry you can still do this route, but without the stops.
This was a fairly fast trip with winds on the beam (but light when in the lee of islands--gives you time to plot and cook).
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