sail close to the wind

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• Received-Pronunciation: /seɪl ˈkləʊs tə‿ðə ˈwɪnd/
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• General-American: /seɪl ˈkloʊs tə‿ðə ˈwɪnd/
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• Australia: Recorded audio is listed in the source snapshot.
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• rhymes with -ɪnd
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Sense 2 (“to behave in a manner on the verge of being dangerous, illegal, or improper”) derives from the fact that to sail an old-fashioned sailing ship close to the direction the wind was blowing from was risky because a small change in the wind direction could fill the sails and push them against the mast, potentially breaking it.

7 source translations are retained for this English entry.

• Finnish: kryssiä — to sail in a direction close to that from which the wind is blowing
• Finnish: luovia — to sail in a direction close to that from which the wind is blowing
• Greek: πιτσυλίζω (pitsylízo) — to sail in a direction close to that from which the wind is blowing
• Māori: ngongo — to sail in a direction close to that from which the wind is blowing
• Portuguese: bolinar — to sail in a direction close to that from which the wind is blowing
• Russian: идти́ о́стрым ку́рсом (idtí óstrym kúrsom) — to sail in a direction close to that from which the wind is blowing
• Finnish: luovia — to behave in a manner on the verge of being dangerous, illegal, or improper