On many occasions, you will engage in sea battles during your journeys. When a naval battle (perhaps the most exciting part of Pirates) is about to begin, you will have to choose which of your ships will be the flagship (the ship that will carry on the battle). A naval battle can end in three different ways: the enemy ship sinking, one of the ships disengaging or the two ships coming head to head. In that last case, if the enemy ship is heavily damaged, the demoralized crew will surrender without a fight. Otherwise, you have to test your fencing skills. While your crew fights the enemy crew, you will have to face the enemy captain. You can choose between three types of attacks and you can defend yourself in three different ways, each defensive move warding you from a specific attack. While fencing is very easy in the levels with a lower difficulty (you can finish the game only with offensive moves in the lowest level of the game), you must perform excellently in defense as the difficulty increases. Fortunately, the game controls are very easy and you will face no problem at all in any part of the game.

Of course, besides fencing you can use your gunnery skills in a sea battle. By using the chain shot you can destroy the enemy's ship mast, immobilize it and make it an easy target, while the grape shot is very effective against the enemy crew. Finally, round shot can cause severe damage to the hull of a hostile ship. Different types of ships require different strategies (i.e the best way to deal with a slow moving Galleon is to destroy her mast with an accurate cannon fire and then - using the grape shop - to reduce her crew. Finally, when your crew outnumbers the crew of the enemy ship, sling aboard and you will capture her without any further fights). Often, the capture of a ship provides you not only with goods and money, but also with specialized crew members, such as gunners (they increase the fire rate), carpenters (they repair damages during a voyage), navigators, etc.

Another way to increase your fortune is to attack the wealthy enemy towns. This option has great dangers (in most of the cases the soldiers who defend the city outnumber your buccaneers) but in a successful attack, the amount of money that will end up in your hands surpasses by far, the money that an enemy ship can provide you. During the attack, the game changes from real time to turn-based. You have to break through the defenses of the soldiers and invade the city. The achievement of a convincing victory rewards you with the option of installing a new government that is friendly to you, otherwise the province will remain under enemy hands.

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