You and your friends all make a living by selling goods amongst a chain of beautiful tropical islands. Sounds great; right? Well; there's a problem. None of you are successful enough to buy your own seaplane; so you all pitched in and bought one together; which means that each day you all have to use the same plane to make all of the day's deliveries – and some of you aren't going to get paid. To make matters worse; the plane is in such disrepair that the instrumentation is broken; the compass demagnetized; and the windshield is covered in cracks; duct tape; and the remains of a few unfortunate seagulls; so the pilot might as well be flying blind...
Each day in Island Hopper; players auction off the Captain's seat; the player who becomes the Captain is in charge of flying the plane for the day; but cannot make any deliveries of their own. To make their deliveries; the other players bribe the Captain to fly to the islands to which they need to go; thereby earning themselves cash. When it's time for the Captain to fly; the Captain must close his eyes; pick up their goods tokens; and attempt to land them in an island's harbor. A successful landing means that players can fulfill their contracts and the captain collects his bribe — but if the goods splash into the sea; you might find yourself under water...