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.

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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

They have therefore but small hold on the water; they do not sail close to the wind, and beating home against it is a long wearisome job.

From A Poor Man's House by Reynolds, Stephen Sydney

In fact the Comédie may remind some of the old nautical laudation of a ship which cannot only sail close to the wind, but even a point or two on the other side of it.

From A History of the French Novel, Vol. 2 To the Close of the 19th Century by Saintsbury, George

To sail close to the wind, in order to approach nearer to an object.

From The Sailor's Word-Book An Alphabetical Digest of Nautical Terms, including Some More Especially Military and Scientific, but Useful to Seamen; as well as Archaisms of Early Voyagers, etc. by Belcher, Edward, Sir