The Expedition is the "Challange" portion of the show, in which the cast is divided into two teams to compete for the buried treasure.

• The Captain and his officers automatically join the Black Crew.
• If there is an odd number of remaining pirates, the Captain, and the Black Crew, gains the extra man.
• Having the extra man may be an advantage, as having more people to row a boat means an extra advantage in speed.
• On the other hand, Having the extra person may bring down a team if the entire team is needed to continue past a certain point.
• The normal pirate crew draws colored shot out of a bag to randomly determine teams.

• With the teams assembled, they must use the treasure map provided to get to the treasure before the other team.

• On some expeditions, a primed trap awaits the expeditions teams. This is called a Sabatoge point.
• The leading team may Sabatoge the other team at this point. Using the Sabatoge springs a booby trap on the other team, buying the lead team a bit of time to look for the treasure.
• A team that takes too long finding a Sabatoge point may endanger themselves by allowing the other team to catch up, minimizing any advantage they would normally have.

• The Expedition ends when one team finds the treasure and signals their victory by firing a pistol.