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Woah, a little trip down memory lane... This post made me think of this: http://www.mobygames.com/game/american-challenge-a-sailing-s...

This was actually quite a reasonable sailing simulator if I remember correctly. Good enough that when I finally got a chance to sail for real a few years later, I knew what I needed to be doing in terms of positioning sails to obtain various points of sail. Of course, navigating without an overhead map being available, and knowing about ropes were two things that I still had to learn the old-fashioned way :)



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