OK Murray, I need you and Sly to blast the rudders off all the galleons in port. With their boats disabled, the pirates won't be able to chase after us when we sail for Dagger Island.
― Bentley to Murray, at Blood Bath Bay's port[src]
The Cooper Gang cannot be followed when they set sail. Using a jolly boat, Sly and Murray must take out the rudders on the galleons in port, then deal with the Harbor Patrol.
Sly and Murray needed to blast the rudders of all galleons in port. Disabling the ships would allow the gang to escape to Dagger Island without being chased.
After destroying the four rudders, the harbor patrol showed up and to destroy its armor, Murray must ram the jolly boat in the patrol boats.
Finally, a big cutter surprisingly appeared and they must attack its weakest part: the mast. Once destroyed the mission is completed.
- When taking out the harbor patrol, it is possible to destroy their boats just by ramming them.