Look out to leeward, a little afore the beam, and you will see one a long way out of the ordinary.
-- Patrick O'Brian, The Wine-Dark Sea, 1993
Two of the most daring flew to the main-rigging, one ascending to windward and the other to leeward.
-- Frederick Marryat, The King's Own, 1830
While the ultimate origin of leeward, first appearing in English in the 1500s, is not known for certain, it contains the Old English hleo meaning "strong." This in turn came from the Old Norse hly meaning "shelter" and "warmth."