Bruce VanSant guide
Anyone who sallies forth heading East from Florida must have Passages South: The Thornless Path to Windward by Bruce Van Sant. It is one of the best guides ever written because of the science it incorporates. Follow the author's advice and you will enjoy your trip much more than otherwise. It is not a geographical guide per se (except where he discusses the D.R. and southern Coast of Puerto Rico) but a passagemaking guide.