Cap'n Snaggletooth wants to retire and hand over his veteran ship The Golden Flounder to one of his crew members, namely to the one who brings him the fullest chests from Treasure Island. And so the pirates let the boatman ferry them to the island to fill their chests with treasure. They must pack as many treasures as possible cleverly into their chests in order to lose as little treasure as possible as payment for passage to the boatman Jewels Jack...

The goal of Treasure Trouble is to hand over as many treasures as you can to the Captain. The game is divided in several rounds. Every player has a treasure chest, which must be quickly filled with treasures but beware because the lid has to fit! After the looting, you may have to hand over some of your loot to Jewels Jack, the boatman.

The player with the most treasures left in his chest wins the round and receives part of the ship. The first player to complete their ship of four parts wins!