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First off, welcome to the game and to the forums! Have some rum!
Now, if you want to board a ship, that ship has to be a flagship. You can tell which it will be because it will have that extra flag symbol over the name of the ship. Once you take down all of the health on that ship, you can use grappling hooks (skill 8 on the cannon) to grab it and tow it to your ship, and then you will have the option of boarding it and defeating the enemies onboard for loot. Hope this helps mate!
-Kat Crestshot
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