Country Dictionary

close to the wind

when one farts and can smell the brown bomb lurking in the back passage,

'that stinks' said jonny 'can you smell that i'm sailing close to the wind, any closer i would have touched cloth'

Close to the wind

(of a sailing vessel) pointed as near as possible to the direction from which the wind is blowing while still making headway.

The experienced sailor expertly maneuvered the sailboat, sailing close to the wind to maximize speed and efficiency.

Sail close to the wind

verge on indecency, dishonesty, or disaster

Here's a sentence using "sail close to the wind":

The politician's campaign ads sailed close to the wind with their negative attacks on the opponent.