on the wind

(nautical) As close as possible to the direction that the wind is blowing.

Japanese Meaning

航海用語として、風が吹いている方向に可能な限り近い角度、すなわち風の方向に限りなく近い進路を指す

The skipper steered the yacht on the wind, keeping the bow as close as possible to the wind's direction.

船長はヨットを風に極力近い方角に操り、船首を風向きにできるだけ近づけた。

Sense（1）

(nautical) As close as possible to the direction that the wind is blowing.