In the first Cartagena game, the players, as pirates, attempted to flee prison by making their way through a tunnel to a boat waiting for them at the end of the tunnel. But simply reaching the boat does not mean they have escaped as re-capture is always possible, perhaps, even likely. They will not be really safe until they reach their Pirate's Nest on Tortuga.

Each player leads a group of pirates to Pirate's Nest on Tortuga.The path leads the pirates through wild jungle and across the waters of open ocean to the island of Tortuga. In addition to the innate perils of the trip are the other pirates, as each group wants to be the first to arrive at Pirate's Nest and will do what they can to slow the others' progress. As soon as one player has all his pirates in Pirate's Nest, he can raise the Jolly Roger and win the game.

The game is a sequel to Cartagena with the pirates trying to figure out what to do now that they have escaped from the prison.