sail close to the wind

US /seɪl kloʊs tu ðə wɪnd/
UK /seɪl kloʊs tu ðə wɪnd/
"sail close to the wind" picture
1.

navigare vicino al limite, rischiare, giocare d'azzardo

to do something that is risky or close to the limits of what is acceptable or legal

:
His business practices often sail close to the wind, but he always manages to stay out of trouble.
Le sue pratiche commerciali spesso navigano vicino al limite, ma riesce sempre a stare fuori dai guai.
You're sailing too close to the wind with those jokes; someone might get offended.
Stai navigando troppo vicino al limite con quelle battute; qualcuno potrebbe offendersi.