Sail close to the wind

In its purely nautical sense, dating back to the 15th century, sailing close to the wind or sailing close-hauled, is a very fine line between rattling along at a good rate of knots and luffing the sails i.e. spilling the wind from the sails and being taken aback because one has sailed too close to the wind. Hence its figurative usage, dating from the early 19th century, when sailing close to the wind became a metaphor for taking a course of action fraught with risk, often expressed as 'close to the wind' without any mention of sailing.