The terms "lee shore" and "windward" or "ward shore" are nautical terms used to describe a stretch of shoreline. A lee shore is one that is to the lee side of a vessel — meaning the wind is blowing towards it. A weather shore has the wind blowing from inland over it out to sea. For example, a person standing on a shore when the wind is blowing out to sea (or any large body of water) is standing on a weather shore. If the wind is blowing into shore from the sea, the person is on a lee shore.
By definition, "windward" is the side of an island where the predominant wind travels from the sea onto the island. "Leeward" is the side of an island where the predominant wind travels from the interior of the island to the sea.
The definition of "leeward" is based on its usage: Adjective: on the side away from the wind; "on the leeward side of the island". Adverb: toward [in the direction of] the wind; "they were sailing leeward". Noun: the side of something that is sheltered from the wind, or the direction in which the wind is blowing; "to the leeward". The traditional nautical pronunciations are the elided forms /ˈljuːərd/[1] and /ˈwɪnərd/, pronounced "loowerd" where the first syllable is spoken very briefly, almost as "l'ward". The literal pronunciations, /ˈliːwərd/ and /ˈwɪndwərd/, are now more common, and "lee" by itself is always pronounced as it is spelled. The pronunciation for the Leeward and Windward Islands and the Leeward Antilles is normally the latter form, with the long "e".
The windward shore is a lee shore for vessels traveling offshore, and that shore is "to leeward" of the vessel, but that does not make it the leeward shore of the island. Although the terms are often confused, "the lee shore" is different from "a leeward shore" based on the reference point from which the shore is viewed. Notice the different articles "the" and "a" — "the" windward or leeward shore versus "a" lee shore. The shore that is a lee shore changes based on the reference point, which is the vessel from which the island or lake shore is viewed, and of which the island or lake shore is in the lee. The leeward shore does not change based on the position of the vessel. This means that the "leeward side" of the vessel and the "lee shore" of the land face opposite directions.
To someone on a vessel, the shore to lee of the vessel is the lee shore, and since that is the shore the wind reaches first, to someone on the shore it is the windward shore. "Lee" historically means "shelter". Standing on the leeward side of the vessel, a sailor observes being blown towards an exposed shoreline by the wind. Here again the reference point from which a shore is viewed determines whether it is the lee shore or a leeward shore. On a lake, the reference point is a body of water, so the windward shore is upwind of the center of the lake. On an island, the reference point is a landmass, so the windward shore is the shore upwind (most to windward) of the center of the island. On a vessel, however, the windward rail is the one the wind is hitting first, or the one most upwind. The same is true regarding an island: the side of the island most to windward is the windward shore.