sailing close to the wind

Verb

sail close to the wind (third-person singular simple present sails close to the wind, present participle sailing close to the wind, simple past and past participle sailed close to the wind)

1. (intransitive) To sail in a direction close to that from which the wind is blowing, while still making headway.
   • As the Syrene vvas ſeen to fall to leevvard in the afternoon, the ſignal vvas made to her to ſail as cloſe to the vvind as poſſible.1781, [Mouffle d’Angerville], “Appendix. Secret Expedition, from 1758 to 1759.”, in J. O. Justamond, transl., The Private Life of Lewis XV. […], volume IV, London: […] Charles Dilly, […], →OCLC, page...
2. (figuratively, intransitive) To behave in a manner that is on the verge of being dangerous, illegal, or improper.
   • But he received only indifferent remuneration, in those days, and found himself to "sail close to the wind," to meet his current expenses.1876, Geo[rge] P. Burnham, “How Reuben Downer Made and Saved It”, in A Hundred Thousand Dollars in Gold. How to Make It. […], Springfield, Mass.: W. J. Holland, →OCLC, page 198