"sailing close to the wind"

The schooner 'Strike' sailing close to the wind near Kingston, Ontario
Creative Commons Attribution Share AlikeThe schooner 'Strike' sailing close to the wind near Kingston, Ontario - Credit: Susan Davis
A phrase meaning to do something dangerous or only just acceptable. The saying comes from sailing terminology, in which boats cannot actually sail into the wind without losing momentum and stopping in the water. Sometimes their helmsmen will sail as close to the wind as possible (also called close-hauling) without losing efficiency – a complicated tactic.