We wasted a full year of childhood development playing games on SEGA Channel as a child, including the popular-with-certain-nerds Pirates! Gold. The game set you as the captain of a pirate ship in the rough-and-tumble Caribbean in the early colonization period. You had a large map to explore and you could sword fight, naval battle, charm, and trade your way to victory. There was even an opportunity to woo various females in order to secure a lovely wife for extra points. And while I didn't play the game on an actual naval warship, a la Alex Roy and a PSP, commenter PatFromGundo came pretty close.
I used to do something like this. I would play "The Sims" while my roommate was having sex with an actual human girl.