The CheckedTwice founders often look for the private islands where they’ll retire when CheckedTwice goes public. (It’s nice to dream, no?) Well this game allows you to live it, and for only about $30.
Puerto Rico allows you to manage your plantation and in-town holdings to amass greatest wealth and curry favor back in Europe. This turn based game was published originally in 2005 and can be played with 2-5 players. The strategy behind it can be fairly complex, and it has risen to the #4 on BoardGameGeek’s rankings. Here’s their description:
The players are plantation owners in Puerto Rico in the days when ships had sails. Growing up to five different kind of crops—corn, indigo, sugar, tobacco, and coffee—they must try to run their business more efficiently than their close competitors: growing crops and storing them efficiently, developing San Juan with useful buildings, deploying their colonists to best effect, selling crops at the right time, and, most importantly, shipping their goods back to Europe for maximum benefit.