sail close to (near) the wind, to

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sail close to the wind

To do something risky or dangerous. If you keep sailing close to the wind, the police are going to arrest you eventually.
See also: close, sail, wind
Farlex Dictionary of Idioms. © 2015 Farlex, Inc, all rights reserved.

sail close to the wind

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.
See also: close, sail, wind
The American Heritage® Dictionary of Idioms by Christine Ammer. Copyright © 2003, 1997 by The Christine Ammer 1992 Trust. Published by Houghton Mifflin Harcourt Publishing Company. All rights reserved.

sail close to the wind

mainly BRITISH
If someone or something sails close to the wind, they take a risk by doing or saying something which almost breaks rules or laws. Max warned her she was sailing dangerously close to the wind and risked prosecution. I have never known a comedy series to sail so close to the wind. Note: If someone sails a boat too close to the wind, they try to sail in the direction from which the wind is blowing, and stop or capsize as a result.
See also: close, sail, wind
Collins COBUILD Idioms Dictionary, 3rd ed. © HarperCollins Publishers 2012

sail close to (or near) the wind

verge on indecency, dishonesty, or disaster. informal
This originated as a nautical expression, meaning ‘sail as nearly against the wind as is possible’. It has been in figurative use since the mid 19th century.
1996 Martin Dove How To Win Any Consumer Competition I like the extra thrill of writing to a tight deadline but sometimes I do sail a bit close to the wind with closing dates.
See also: close, sail, wind
Farlex Partner Idioms Dictionary © Farlex 2017

sail close to the ˈwind

behave in a way that is almost illegal or socially unacceptable: She’s been late for work three times this week, which is sailing close to the wind, I think.
See also: close, sail, wind
Farlex Partner Idioms Dictionary © Farlex 2017

sail close to (near) the wind, to

To come close to breaking a law or approaching impropriety. The analogy to sailing dangerously close to the wind began to be made in the nineteenth century. Coleridge’s son Hartley, in a critical edition of the plays of Massinger and Ford (1840), used it: “Her language sails a little too near the wind.” It is heard less often today.
See also: close, sail
The Dictionary of Clichés by Christine Ammer Copyright © 2013 by Christine Ammer
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References in periodicals archive ?
Everton are a club who tend to sail close to the wind where transfer deadline day is concerned, but this year the feeling is that they have got their deals right, even if they did leave it pretty late.
Our correspondent investigates if there has been any progress on this as yet of if the banks are continuing to sail close to the wind.
It encourages jockeys to sail close to the wind, and the fact that Ahern got a two-day ban for careless riding tells you he did, if not right into it.
"Walking in at half-time we only had one sub so you know you're going to sail close to the wind.
If, for purposes of illustration, we entertain the English idiom 'to sail close to the wind', the AND explanation of estreit beiter as 'to act carefully' seems quite close to the mark but lacks the reference point of the idiom, the prevailing wind in the concrete application, ethical standards in the social context.
Raeside continued to sail close to the wind when he barged into Lloyd Young but the ref only issued a warning.
Despite his troubles over his notorious public denouncement of Norman Lamont - a broadside which, for a time, derailed his career - our Julian still loves to sail close to the wind. Only last month the outrageously camp funnyman caused chaos on Ian Wright's chat show when he suddenly "outed" a well known personality while being interviewed.
Coach Nathan Brown has his side working as a well-drilled defensive unit once more but they continue to sail close to the wind with their discipline.