For those in the Virgin Islands, everything south and east is “Down Island.” This means two other island groups in the chain, the Leeward Islands, and the Windward Islands. A down island charter is more oriented towards the sailing aspect of the vacation, and has the possibility of experiencing several national cultures, while a Virgin Islands-based charter is oriented toward water sports, beaches, and diving, in addition to the sailing. For folks living in the Grenadines, our office is “Up Island.