To sail in a direction close to that from which the wind is blowing, but still making headway
To behave in a manner that is on the verge of being dangerous, improper or illegal

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    "sail close to the wind." Phrases.com. STANDS4 LLC, 2024. Web. 19 Apr. 2024. <https://www.phrases.com/idioms/sail-close-to-the-wind>.

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