If a sailing ship sails too close to where the wind is coming from, the headsails will start to flap a little; known as luffing. The ship would then slow down and not sail efficiently. If the ship goes a little closer to the wind there's a danger that she will go through the wind and would end up heading the wrong way with the sails incorrectly set. A serious problem. It's best to sail close enough to the wind that the sails are just off the point of flapping and you'll get away with it.
By SailingQuiz November 2019 Category: Nautical Saying
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Definition of the nautical phrase "Sailing too close to the wind".