The Clothes of a Pirate is longer than any quest we have completed so far, because we have to find several items for Largo (the quest-giver).
To start this quest, we have to visit the prison tower near Puerto Sacarico, where Carter (Sturdy Clothes quest) guards a prisoner named Largo. If we approach Largos cell we can discuss with him and activate two new quests (The Clothes of a Pirate and Freeing Largo).
While playing the first quest, we will also be able to complete the latter.
Carter took all of Largos possessions. It seems hes sold some of them, but he cant have sold everything .
Carter sold Largos bandana to the warden Riley. I can find Riley on the sugar plantation.
Carter kept Largos black pearl for himself. If I want to get my hands on that earring Ill need to learn to pickpocket. Then Im sure Largo will have some information for me.
To get Largos boots back, I have to sneak into the barracks at night.
200 Glory Points for the quest + additional Glory Points for defeating Riley and pickpocketing Carter.
Two of the items required by Largo can be found in Puerto Sacarico, and to avoid a trip to the cotton plantation, we should head back to the town and sleep in any bed, until evening.
When the night falls over Puerto Sacarico, we go straight to the town center and locate the barracks. Inside we will find Largos worn-out boots.
To get the boots, we make sure that the guards are sleeping, and we sneak inside, avoiding Osorio the cook.
The boots are on the right side, in front of a locked chest.
We get them and exit quickly. The second item required by Largo, is his bandana.
Largos Bandana is in Rileys possession. If we play this quest during the evening we can find Riley, in Puerto Sacarico, having dinner, with other guards.
When we talk to him, we can take the item; however, how we approach the subject is very important.
If we intimidate Riley (assuming that our intimidation skill is above 10), we can get the bandana right away, without a fight.
If we insult Riley, he will draw his sword, and we must defeat him. As soon as he is down, we grab the item, because the guards wont interrupt us.
The third option is to move the conversation to another subject, and in this case, our hero wont be able to re-open the subject.
If this happens, we have to wait until morning, and travel to the sugar plantation (north of Puerto Sacarico). Next, we look for a slave named Asad (A Hungry Slave quest should become available now), and Riley will automatically become aggressive.
We argue with him, and then take him out to retrieve the bandana. The third item is a shirt.
Largos Leather Shirt
Largos shirt can be bought from his guard, Carter.
To get it, we must travel back to the prison tower, after we complete the Sturdy Clothes quest.
The shirt costs 150 gold and we make sure we buy it, as soon as we have enough money.
Once we get the shirt, we keep it in our inventory and continue our search for the last item, which is a Black Pearl.
Largos Black Pearl
The final item is Largos earring, which contains a pearl. Unlike all other items, to get the last one, we must spend a considerable amount of gold (1000), because we need to steal the item from Carter, who guards Largo.
To learn the pickpocketing skill we need to increase our Cunning talent to 2, and then talk to Largo who will teach us how to pickpocket.
During the conversation we also learn that Carter likes to drink. We make sure we get some grog from Osorio, the cook, and then we return and offer the grog to Carter.
We grab the earring, and the quest will be complete; however we keep all items we have received.
Note: Largos items can help us complete additional quests, such as OBrians Treasure Map and Freeing Largo. We keep the items until these quests have been completed, then we can return them to their owner.