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Captain Crawfish has a ship with the speed and cannons of a Phoenix Warbird. Attacking him with anything less has very, very little chance to succeed. His ship will repair itself as yours does (with the Shipwright).
When you have found and merged the 5 map pieces, and the new island Skullduggery appears, that is where Captain Crawfish is easily found. When you have a Phoenix Warbird, the Shipwright, and the Cannoneer, you are a match for him. He will not actually sink, but sail away when defeated.
(see related question)
*You can reduce the time it takes to get the Phoenix Warbird by buying each larger class of ship when you can afford it. You may skip one or two if you are earning large salvage from sinking sea creatures and pirates.
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How do you dig up the treasure on Skullduggery Island?
Once you have the 5 pieces of the map, you still have to drive off Captain Crawfish, which requires a powerful ship and some skill at shooting the cannons. Once he is gone, go to see the Governor on Fort Ridley, and he will give you the treasure location and a bone shovel. Then you can travel to the hidden island (Skullduggery) and dig it up.
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