I like playing video games and have found a couple of them with sailing components. Black Flag was fun, but sailing in GTA is pretty boring. None have been very good, as Bobby points out. I figure the physics engines are very basic and the game developers aren't sailors, nor do they expect their target customers to be. It's too bad, because there's a unique action to sailing that would make it a good video game adventure.
I didn't know about the games mentioned above. I'll have to keep an eye out for them.
My favorite sailing game is actually a board game called 'Wooden Ships and Iron Men'. It involves establishing a wind direction and speed each turn. The player writes down his planned maneuvers in secret. Player's distance traveled are limited by angle to the wind. The goal is to position yourself for a broadside to your opponent and sink them. Your best maneuver is to "cross the 'T'", allowing you to fire a full broadside at your opponent while limiting or completely avoiding their fire at you. You play it with little plastic models on a gridded playing board.
With these newer 'go anywhere' video games, a good sailing adventure would be cool.
-Will (Dragonfly)