Usually means: Sailing against the direction of wind.
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We found 4 dictionaries that define the word to work to windward:

General (4 matching dictionaries)
  1. to work to windward: Wordnik
  2. To work to windward: Dictionary.com
  3. to work to windward: FreeDictionary.org
  4. To work to windward: TheFreeDictionary.com



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