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I agree with Captain Sea, usually forts are the best bet. Fort Charles (Port Royal), Fort Dundee (Padres Del Fuego), and Fort Kingshead (Kingshead). I was able to level up my cutlass from 10 to 15 very quickly at Kingshead.
FYI, levelling up your dagger to get the skill that lowers the cooldown rate between combo moves is a GREAT way to level up your cutlass then. In some cases, the enemy doesn't even get a chance to react or strike you.
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