Chain of Fools
At the far left the Bandido is a proxy for the Mermaid.
I didn't have time to find the Saragoza so the Reconquistador is a proxy. I don't have the Song - the Hai Peng is another 2 masted junk from POTC.
Since the middle island was already empty and the northeastern island was closer than the southern island, the Raven's Neck was Hidden Cove'd immediately so she could start transferring gold home. After Gilbert sacced an oarsman the Oarsmen Inflation fleet had 13 gold on their home island at the end of turn 1! After swapping Davy Jones' Key the Raven's Neck island contained three 2's and a 5.
The Raven's Neck and Captain Jack Sparrow only needed to transfer one 2 (+3=5 total gold) home in order to gain an 18-0 victory!
As always, thanks for reading!