sail close to the wind

Related to sail close to the wind: off the wind

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.

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.

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.

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

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

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
See also:
  • sail close to (near) the wind, to
  • close to the wind
  • too close for comfort
  • too close to call
  • come close
  • close by
  • close to (one's) heart
  • close to your heart
  • be close to the mark
  • be close to/near the mark
References in periodicals archive
Rooney did sail close to the wind at times, picking up an early booking for a lunge on Everton goalscorer Tim Cahill and then expressing his frustrations to referee Howard Webb in no uncertain manner when he believed Lee Carsley had aimed a stamp at him as the pair duelled at a drop-ball.
Football: 'MY BATTLE WITH THE BLUES FANS' - but victory over former club special says Rooney
But while he was free from a jail sentence or a fine, his decision to 'sail close to the wind' with his batch of 'angry and unpleasant' letters has left him around pounds 10,000 out of pocket, after the judge refused to award the former councillor full costs, summarising that he had brought the legal action on himself.
Clywch letters 'not contempt'
These days, you need a degree in rocket science to follow the ever-changing offers being made by the various mobile phone companies - some of which sail close to the wind as far as truth is concerned.
A Spoonful of Sugar: No call for this mobile
They sail close to the wind particularly in the ruck and at the offside line.
Take Toulouse to bag first points
Mr Norton (left) might often sail close to the wind, but his risque ribaldry has a huge fanbase.
TV: 5 reasons to turn on
The fact that he likes giving the impression to virtual strangers that he has no problem with the idea of a little sail close to the wind, or that he enjoys the company of ladies who are not, and have never been, members of the Salvation Navy, is a matter of total irrelevance.
Paul Haigh: A sting and the tale that fails to uncover corruption
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.
Comedy: Clary, Clary quite contrary..