To behave in a manner that is on the verge of being dangerous, improper or illegal
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Submitted on July 07, 2010

Additional definitions for 'sail close to the wind':

sail close to the windTo sail in a direction close to that from which the wind is blowing, but still making headway
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    "sail close to the wind." Phrases.com. STANDS4 LLC, 2024. Web. 28 Mar. 2024. <https://www.phrases.com/phrase/sail-close-to-the-wind_14714>.

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