sail close to the wind

Idioms  

1. Be on the verge of doing something illegal or improper, as in She was sailing pretty close to the wind when she called him a liar. This term alludes to the danger incurred when literally sailing too close to (that is, in the direction of) the wind. Its figurative use dates from the first half of the 1800s.

---

Example Sentences

Fox, who hosts a weekly show on GB News and made the remarks while appearing as a contributor on Wootton's programme on Tuesday, does usually "sail close to the wind", the chief executive said.

From BBC • Sep. 29, 2023

Of course, politicians, like most humans, at times sail close to the wind, and sometimes for understandable reasons – personal, security, confidentiality.

From The Guardian • Dec. 31, 2016

"We must sail close to the wind now, Count," said the ever cheerful Paul to the despondent Dane.

From The Story of Paul Boyton Voyages on All the Great Rivers of the World by Boyton, Paul

The wind was very unfavorable to a craft that was unable to sail close to the wind.

From A Journey to the Centre of the Earth by Verne, Jules

It would then be necessary to sail close to the wind!

From Dick Sand A Captain at Fifteen by Verne, Jules