i like Legend of Two-Toed Tobias not due the quest layout, i like it cause it feels like a pirate story and sadly the full quest package fails to give the real pirate feel.
Prove Your Worth -> Stairs and puzzle? No very piratish...
The Scoundrel's Run-> More Indiana jones stuff related
Fire Caves -> hmm pirates and volcanos dont mix.
So, my vote will go for Tobias (a ghost pirate) or Guard Duty (pirates asaulting a ship).