Remember the prisoner who was being kept in the courtyard during the very first quest in the game, the one who taught you how to sneak (if you paid him, that is?) Well, he has been brought here to Tacarigua as well, albeit for very different reasons. Speaking with Pedro in the city courtyard will reveal that a prison guard is selling clothes up at the prison tower down the dirt path leading to the north. The tower won’t be hard to find at all; it’s basically the first thing you see when you leave town to the north. Speak with the prison guard and ask him about purchasing some clothing. This is an alternate way to get the clothes necessary for obtaining the map from Di Fuego, if you haven’t done so already.

Speaking with Largo in his prison cell to the right will reveal the origin of these clothes. Turns out they were all his, and the prison guard nicked them and decided to sell them on the side. Largo just wants his clothes back now, a perfectly reasonable thing. And maybe his freedom, too. But hey, one thing at a time. Before you decide whether or not to free Largo, you will have to go out and find his clothes for him. You will have to collect four items and then return them all to Largo at the same time. He will only accept them all back together, once you have collected the lot of them.

The four items you will have to collect are as follows: Pirate’s Bandana, Worn-out Shoes, Leather Shirt, and Black Pearl. You can ask Largo about each individual item and its current whereabouts, as far as he knows, so go through each of the options to get a few hints as to how to proceed.

As it turns out, the prison guard will still be in possession of the Black Pearl item. It will be in his pockets somewhere. In order to get it out, you will have to learn how to pickpocket. Luckily, this is knowledge that Largo is willing to share, for a price that is. Never mind that he is sitting in a jail cell; apparently, he will still need money. If you go through with the escape plan in the next phase of the quest, this money will help him buy his way out of the area. Learning how to pickpocket is probably the most restrictive part of this entire quest. Learning the skill is almost prohibitively expensive, at a whopping 1,000 gold price. You will also need to be at least level two in Cunning. Once you meet the requirements, head over to Largo and ask him to teach you a thing or two about pickpocketing.

After learning and practicing the skill, you will have to make a move on the prison guard. Largo will tell you that the guard is especially fond of grog, almost to a debilitating extent. Get him drunk, and that Black Pearl is as good as yours. If you don’t have any grog on you at the moment, look right next to the guard, to the right. There will be a small chest here that contains a bottle of grog. If by chance you have already looted this resource and used it for yourself, note that you can also get some from Osorio, the cook from the Kitchen Help quest, but you will have to shell out even more Gold for it, and at this point that’s probably the least appealing of all the options. When you have the grog in hand, head back to the prison guard and speak with him. Offer him a drink, and he won’t be able to refuse. He’ll get drunk, and you can pickpocket the pearl from him.

While you have the Black Pearl in your possession, note that you can use its stats (a +1 boost to your Cunning stat) to help you complete other missions. In particular, you can throw it in the pool during a drinking contest for a treasure map in the quest O’Brian’s Treasure Map, and you can convince Stone to give you a free lockpick later on, when attempting to free Largo. Use this to your advantage later.

The second item is a pair of Worn-out Boots. This will be a relatively easy item to obtain. You can only find it inside of the barracks, in the main square. The barracks will be sitting directly to the right from Di Fuego’s mansion in the square, so look here if you are having trouble finding it. You can get the boots at any time of the day, but you’ll have to be more careful during the daytime. It’s best to sneak in at night, and sneak in you must. If you can’t sneak, you’ll have to learn first. If it’s daytime, find a bed to sleep in until midnight, when the soldiers will take a rest. Wait until all of the guards are asleep, and sneak inside of the building’s entrance, hugging the wall. Make sure that nobody is there to witness your infiltration, or you will be caught and have to repeat everything. The boots will be sitting right out in the middle of the floor, so don’t hesitate to grab them up once the coast is clear.

The next item on the list is the Pirate’s Bandana. This will be in possession of Riley, the boss of the sugar plantation from earlier. Head back to the plantation and speak with him. You will automatically mention the bandana. The next response is key. Whatever you do, DO NOT back out of this conversation and forget that you mentioned the bandana. If you do this, you will not be able to go back and ask for it again in any other way. If you use the second or the third answer, you will find that you have insulted Riley. This will prove to be a pretty bad idea, as he will immediately and abruptly attack you. This attack will be pretty unexpected, so you will have to fumble to draw your blade or gun. You will now have to defeat Riley. He might be annoying, but he’s not overly tough. Just keep on guard, blocking his attacks, and retaliate with a quick series of strikes of your own before returning to a guarding position. When you defeat him, you’ll get 50 Glory points and the bandana. Finally, if you can manage to Intimidate Riley (you’ll have to have at least 10 points into Intimidation) he will give you the bandana peacefully. It is key, however, that you maintain a threatening façade even when Riley goes at you for a second time, or you will end up backing down and provoking him into a fight anyway.

If you ended up backing out of the conversation and now can’t figure out how to get the bandana, don’t worry. There is still another way to get the bandana, by provoking Riley into attacking you. Speak with the slave at the plantation. Riley will warn you when you do this to not attempt it again. Don’t listen to him. Speak with the slave again, and Riley will attack you. In this way, you can lure him into a fight just as you could with the second and third dialogue options. Beat him down and take the bandana from him after the fight.

The final, and easiest, item to obtain is the Leather Shirt item. This can simply be bought right off of the prison guard for 150 Gold. Once you have collected all of the clothes and returned them to Largo, you will receive 200 Glory points. Keep in mind that, as mentioned earlier, having some of Largo’s items for just a little bit longer can prove helpful. For this reason, a few other quests will be covered before we get to freeing Largo, which will necessitate returning his clothes to him first.