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Only the Light Frigate and the Light Galleon have broadside cannons, the Light Sloop doesn't. So to level up your sailing, you have the have the light frigate or the light galleon.
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Open Pirate
Jack Sunshot: Level 17 Notoriety, Level 6 Cutlass, Level 6 Pistol, Level 8 Cannon, Level 7 Sailing, Level 5 Voodoo Doll, Level 5 Dagger
Test Pirate
Jack Sunshot: Level 15 Notoriety, Level 7 Cutlass, Level 5 Pistol, Level 8 Cannon, Level 4 Sailing, Level 4 Voodoo Doll, Level 3 Dagger
Member of the Bad to the Bones: http://www.piratesonlineforums.com/f...ead.php?t=1342
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