Definition, Meaning & Synonyms

to-sail-close-to-the-wind

idiom

/tuˈseɪl ˈkloʊs tə ðə wɪnd/

Definition

To behave in a risky or daring way, often pushing the limits of what is acceptable or safe.

Examples

He tends to sail close to the wind with his financial dealings, often testing the legal limits.
In her career, she has learned to sail close to the wind, always pushing for what she wants without fear.

Meaning

This phrase originates from nautical language, referring to sailing a ship as close to the direction of the wind as possible to gain the maximum speed. Metaphorically, it means to take risks or act in a way that might lead to trouble or problems, yet without crossing a line.