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Attacking pirate hideouts is a great way of making money, first get a good convoy and mark all of the ships as warships then go to the hideout and attack it, you will probably face a convoy so capture that. Then you will have to attack the defenses, the best way of winning is lodging your ship near one of the beaches and firing Large Cannonballs. After you will probably duel with the pirate, just right click on your body whenever he tries to attack and after he's depleted on muscle, attack him constantly (add in a few special attacks too) after you receive a reward but it's not over, go to any governor and he'll give you a reward.