Perhaps the earliest "realistic" sailing game, American Challenge pits your mettle and sailing skills against other computer-controlled opponents in sailboats or motorboats. Wind direction, waves, and weather effects all play a part in this excellent sim, which is as accurate as it could get given hardware in 1986 :)
People who downloaded American Challenge: Sailing Simulation, The have also downloaded:
Campo's International Rugby (a.k.a. International Rugby Chal, Paragliding (a.k.a. Paraplane), American Gladiators
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