Sid Meier, best known for his epic computer strategy Civilization series has done it to me again. Meier is the master of the "just one more turn" type of game where you're playing it and every few minutes you say to yourself "one more turn, then it's bedtime". Before you know it the sun's up.
Pirates is an open-ended game that puts you at the helm of a sloop through mutiny at the age of 18. Your parents have been thrown into slavery by an evil landowner but you escaped and now, at the helm of your captured vessel, it's time for you to take your revenge.
If you want to. Or you can become an honest merchant running spices from Havana to Port Royal. Or you can become a black-sailed pirate terrorizing the Carribbean. Or you can hang out in taverns getting in sword fights and buying maps to buried treasure from shadowy strangers in back rooms.
Occasionally you'll get a lead on where your family is held but pursuing that angle of the game, like every other angle of the game, is strictly optional.
Your career is tracked by the game in a variety of ways. How many treasure chests have you unearthed? How many family members freed from servitude? Have you served any of the colonial powers loyally enough for a military commission? (And hilariously, the answer to this is often yes multiple times- my current character is a Captain in both the Dutch and British fleets, the uniform he wears varies according to the port he's in).
How wealthy are you? This is rated in terms of gold and land, which is usually bestowed upon you for loyal service to one or more of the colonial powers.
How many governors daughters have you romanced?
At the end of your career, all these things will be tallied and your career as a pirate judged.
I can't recommend this game enough. It's addictive. It's fun, it's light hearted. You could even technically play it in small doses, though I'm not sure why you'd want to.