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No, with skillful use of sails and maneuvering you can go any direction, even into the wind: https://en.wikipedia.org/wiki/Tacking_(sailing)

That applies to any sailing ship, whether it is manned by pirates or not, of course.



It’s often described that way, but tacking doesn’t really let you sail directly into the wind.

Instead you combine two vectors which on net result in the ship moving in the direction you want on average. But, with noticeable limitations if you also want to avoid obstacles etc.


The flags wouldn't be blowing straight to the bow of the boat tbough. On a tacking course, they'd be blowing towards the stern +/- 20 degrees.




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