What does "windward" mean?

Windward: The point or side from which the wind blows; as, to ply to the windward; -- opposed to Ant: leeward. To lay an anchor to the windward, a figurative expression, signifying to adopt precautionary or anticipatory measures for success or security.

Additional senses

  1. 2.Situated toward the point from which the wind blows; as, the Windward Islands.
  2. 3.Toward the wind; in the direction from which the wind blows.

Sources