sail close to the wind

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sail close to the wind (third-person singular simple present sails close to the wind, present participle sailing close to the wind, simple past and past participle sailed close to the wind)

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