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There is only two ways to complete this portion of the SvS quest.
1. Join a crew and sail with a player on his/her ship. Use your cannons to inflict damage on the opposition.
2. Launch your own ship, stop in the middle of battle, man a cannon and inflict damage on the opposition.
From experience, option 1 is your best bet.
As for the second part of your question, look for the jewelry and tatoo quests if you haven't completed them. Other than that, the only thing left to do is level up your pirate's different weapons.
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