The only way I can think that this would be possible is if the wind was blowing directly onshore?
Edit: thanks for all the well thought out replies. I think I’ve got it figured out know, I’ve always Been a bit confused about ships tacking into to wind and I think the key thing I was missing was the sail being using like as an airfoil creating pull, used in tandem with with the fins/keel .
In: 341
Sails are never fully flat, but slightly curved. Turning the sail sideways to the wind the wind then flows over both sides of the sail. It has a long path on the outside of the curved sail, and a short path on the inside of the sail. The “faster” bit of air leaves underpreasure where new air is sucked into.
Imagine standing on a skateboard with a massive vacuum cleaner pulling you forward.
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