Leeward and Windward A boat's leeward side is the side that is or, when she is head to wind, was away from the wind. However, when sailing by the lee or directly downwind, her leeward side is the side on which her mainsail lies. The other side is her windward side. When two boats on the same tack overlap, the one on the leeward side of the other is the leeward boat. The other is the windward boat.