You and your friends all make a healthy living by selling goods amongst a chain of beautiful tropical islands. Sounds great, right? Well, there's one problem. None of you are successful enough to purchase 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 whoever is flying might as well be flying blind...

Every 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 is unable to 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 travel to, thereby earning themselves cash. When it's time for the Captain to fly, the Captain must close their eyes, pick up their goods tokens, and attempt to land them in an island's harbor. A successful landing means that players are able to fulfill their contracts and the captain collects his bribe — but if the goods splash into the sea, you might find yourself under water...