1. Is this turn based or real time?
2. How do you know if you won? What is the goal of the game? How do you know you beat it?
1) Real time.
2) There is a campaign. Essentially, the end of the game is when you've built up enough businesses to peacefully integrate Cayman into your own little "colony." -- This is for the Trader campaign. There is another one, Adventurer, which is more of a pirate campaign that I never tried.
However, after that mission, you can continue to play the game as you wish. I'd say it took me roughly 10 hours to "finish," but that is just touching the ice berg of what you can do in this game. Hope that answers your question.
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