Most all sailors heading south for the Caribbean have this straight-talking book aboard and have studied it well. Not a cruising guide per se, Passages South takes the thorns from the "thorny path to windward" with explicit illustrated discussions of passage-making techniques for particular islands. It also has substantial shoreside information about Puerto Rico and the Dominican Republic, where the author lives. You will as well find an amusing section on how to master "Spanglish". See book reviews by sailmiami.com, Sailing Breezes and English cruising association.
Whether you escape west to the Pacific, east to the Mediterranean or south to the Caribbean, read this book first. After a half century sailing and cruising islands worldwide, the author gives you advice for finding your boat, for sailing there, wherever you define your 'where', and strategems for successful living in the islands of the trades. Among the tricks you will learn: Feints to use with brokers and outfitters · Devices to get the jump on the weather · Tactics for navigating chains of islands · Ruses to thwart ceaseless winds and wild seas · Wiles for the aging single hander · Ploys for health and prosperity in the tropics · Dodges to duck thieves, con-men, venal officials · (click here to download pages 92-93.)
Now out of print, you will find this guide book folded into Passages South and The Cruising Guide to the Virgin Islands by Nancy and Simon Scott.