There is a difference between the windward and leeward side of the island and a windward and leeward shore. The difference is actually your reference point, in other words are you on land or on a boat. From Wikipedia:
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, if you were standing on a beach, looking out to sea with the wind at your back, you are standing on a weather shore. If the wind is blowing at you, you are on a lee shore.
The "lee" of a boat is the side that the wind touches last as it crosses the boat; in the diagram it is left or port side of the boat. The boat in the diagram has a lee shore to its west. In the diagram, the other side of the island, to the far west, has a weather shore. The wind blows over the shore as it heads to sea. This wind, because it blows from east to west, is called an "easterly" wind. This is because the source of a wind is more ascertainable or knowable than its destination, so winds are named for their source.
