The phrase is often used metaphorically to describe risky actions in various aspects of life. She always sails close to the wind with her aggressive business strategies.
Pro Tip 2/3
Negative Connotation
The phrase may suggest a negative judgment, implying that someone is irresponsible or reckless. His habit of always sailing close to the wind finally led to his downfall.
Pro Tip 3/3
Context Sensitivity
Use the phrase where the context hints at risk-taking; it might confuse in a literal or safe context. Taking that shortcut through the woods at night? That's really sailing close to the wind.