Caribbean and Leeward Islands
Centuries ago, early Spanish colonizers coined the terms “leeward” and “windward” about the Islands of the West Indies spanning from Puerto Rico to Grenada. In the days when sailing vessels were the only mode of transport, trade winds blowing from the northeast to the southwest determined favorable routes.
In island terms, the “leeward side” is the side protected by the elevation of the island from prevailing winds whereas the “windward side” is the side subject to those same winds. Loosely these phrases correspond to “upwind” and “downwind” in sailing terms – a windward vessel should always give way to a leeward vessel.