to windward

Idioms  

1. Toward an advantageous position, as in We were hoping to get to windward of the situation. This expression transfers the nautical meaning of the phrase, “move in the direction from which the wind blows,” to other kinds of undertaking. Its figurative use dates from the late 1700s.

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Example Sentences

“The boat barely sailed to windward, but off wind and reaching, it was superb,” he recalled to me.

From Slate • Jul. 22, 2025

“Princess Panics-a-Lot” is the teasing moniker that Stuart would gently bestow upon Pat whenever she would get anxious that, beating to windward, we were heeling too much and might tip over.

From Washington Post • Nov. 2, 2017

I was two years old, hoisted on the shoulders of my father, for whom the view to windward was neither openly nor latently sublime.

From Salon • Jun. 3, 2013

He admits his yacht is weakest with the wind astern but adds, "she's a bear cat to windward."

From Time Magazine Archive

If your ship can’t claw off, then you’ll heave an anchor to windward, to try to hold the ship where she is.

From "Carry On, Mr. Bowditch" by Jean Lee Latham