Windward (French - "au vent", Spanish - "de barlovento") is the direction from which a present wind is blowing. The side of a ship which is towards the windward is the weather side, known in some quarters as the "high side".
In general, the pronunciation is "looard" and "windard" but that is nowadays, rather old-fashioned. In any case, the pronunciation for the islands of the Lesser Antilles is Leeward and Windward respectively.
The terms "leeward" and "windward" refer respectively to what a game stalker would call down-wind and up-wind. The terms are used by seamen in relation to their ships but also in reference to islands in an archipelago and to the different sides of a single island. In the latter case, the windward side is that side of an island subject to the prevailing wind, and is thus the wetter side (see orographic precipitation). The leeward side is the side protected by the elevation of the island from the prevailing wind, and is typically the drier side of an island. Thus, leeward or windward siting is a important weather and climate factor on oceanic islands.
In the case of an archipelago, "windward islands" are upwind and "leeward islands" are the downwind ones.
Main article: Sailing
Windward and leeward directions are important factors to consider when sailing a sailing ship, though the terms have largely fallen out of use in favour of "head-to-wind" and "downwind", see points of sail.
For warships during the age of sail, windward and leeward directions were important tactical considerations. A square rigged warship often tried to enter battle from the windward direction (or "hold the weather gauge"), thus gaining an important tactical advantage over the opposing warship – the warship to windward could choose when to engage and when to withdraw, the opposing warship to leeward could often do little but comply without exposing itself unduly. This was particularly important once artillery was introduced to naval warfare. The ships heeled away from the wind so that the leeward vessel was exposing part of her bottom to shot. If damaged between wind and water, she was consequently, in danger of sinking when on the other tack. See Spanish Armada.