Hi Brad, I've sailed almost that
route and I would do it that way: Starting from St-Thomas, first stop to Fajardo, Porto Rico: A good place for provisionning,
boat equipment and
repairs,
fuel etc. From Fajardo straight East, for 20 miles and then NE ranging the island chain at a good distance (to avoid local traffic and the flow of
cruise ships at night), but with always a port of refuge at hand in case of bad
weather. Next stop:
Nassau. An easy and very secure harbor in most
weather. Than from
Nassau To the berries Island and then on to North Rock across the
Bahamas Bank and then across the
Gulf Stream to Ft Lauderdale or anywher else on
Florida Coast. May would be a good time to go, but you still have to watch for a late norther, or an odd tropical wave(I had an unannounced really bad one). But in fact you can stop in some
Bahamas Island - Turk & Caico, San Salvador, Some
Exumas. Carry Bahamas
charts, and good guides to help you through the pass to safe harbors.