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(Thanks Vortfu of Oggok for this writeup!))

Aboard the Smarmy Sprocket, talk to Master Chief Gearspanner and he will get you to check that the
crew are ready to get under way.

Talk to Smith the Cook, and arrange the crates correctly for him. Move
the 'extra large' and 'very small' crates to one side of the ship, and
the other crates to the other (as far as they will go). Talk to Smith
again and he will be ready to go.

Talk to Greedu the Cabin Boy and he will have you plot the course by
the stars. This seems to be random each time, so read the notes and
the tome then plot the course into the navigator next to the Master
Chief accordingly (or just guess the directions until you're correct).

Talk to Bosun Patches and repeatedly kick the sail engine until it
starts up and Bosun is ready to go.

Talk to Master Chief Gearspanner and tell him the crew are ready to go.

Pull the anchor lever between the Master Chief and the navigation
system to go to the Prison of Admiral Grimgadget.

Once you're on the island of the "Prison of Admiral Grimgadget", fight
your way into the prison at the center of the island and find Admiral
Grimgadget in a jail cell (who will give you the 'Save the Pirates'
quest).

The 'Save the Pirates' quest should give up a nice bounty for mid 20
lvl groups, though the "Prison of Admiral Grimgadget" is not a nice
place to solo at lvl 20 :(