A pirate I want to be[edit]
Once Rottingham has stolen the map and your crew has proven themselves to be useless, they start singing. No matter what choice you pick, they always have a rhyme for it. Unless you pick the line with the unrhymeable word "orange".
Regrettably, this section is entirely omitted in the non english versions, skipping right ahead to the ship combat.
[edit]
Once the song is over, it's time to take back the map. But in your current state you have no chance against captain Rottingham. You will have to build up power by defeating lesser pirates, stealing their loot and buying new cannons to climb the ranks until you are ready to take on Rottingham.
If you want to change the difficulty of ship combat just ask Haggis. He will be happy to increase the difficulty, and with a little begging he will lower it too.
First you need to pick a ship to fight on the map. If you wait a bit more ships will appear, but the one you should take on next will appear first. Once selected, a sea battle begins. The general tactic is to put your broadsides on the short end of the other ship and fire without them being able to fire at you.
Once you've won the sea battle it's time for the boarding and sword-fight. You begin with initiative and say an insult. The opponent will then have a chance to reply with a counter-insult. Should the opponent have the correct counter-insult they will take initiative, otherwise you keep it. The same applies in reverse, if the opponent has initiative you get to reply and have a chance to take back initiative.
The winner of the sword fight is determined by who wins the most volleys.
You will automatically learn insults and counter-insults that you hear. Each pirate knows a different set of insults and counter-insults, so don't hesitate to go back to previously defeated pirates to pick up new lines.
Once you've defeated a pirate you should sail back to the harbor and visit Kenny. Kenny have had a career change and is now selling cannons. He will be happy to let you trade in your previous set of cannons each time, so you can successively upgrade to the top model as you defeat pirates.
When you are ready, take on Rottingham. As fans of the series would expect, insult sword-fighting with him is a bit different, he always has initiative and uses his own set of insults. However, your counter-insults still work, if you figure out which one matches his new insults. Defeat him and you will be able to move on to your destination.