Windward/ˈwɪndwərd/ Definition 1 of 3Pro Tip 1/3Sailing Context The term is often used in sailing to describe a boat's position relative to the wind. Keep the sail trim as we head windward. Pro Tip 2/3Weather Influences Windward areas often receive more rain and have cooler climates than leeward sides. The windward side of the island is lush and green. Pro Tip 3/3Hidden Obstacles When moving windward, be aware of obstacles that the wind might be pushing you towards. We steered carefully windward, avoiding the rocks.