This quest is the precursor to the O’Brian’s Treasure quest, in which you use the titular treasure map to seek out the treasure for yourself. Just like the last quest, in which you fought with Hank to secure Holly’s freedom (and your 100 gold,) this one will begin in Booze’s Tavern in the pirate hideout. Look for O’Brian in the tavern and speak with him to kick things off. He will be one of the pirates who is standing up rather than sitting at the bar. In his drunken state, he will tell you two different things, both important. First of all, he will tell you that he recently buried a treasure chest with riches in it. That will be your ultimate objective during this quest. Second, he will invite you to take him on in a drinking contest. Agree to the contest.

When agreeing to compete in the drinking contest, you will have two choices. You will be able to play the game as a simple time killer, with nothing on the line, but that’s no fun. You will want to choose the second option: playing for cold, hard cash. You can win 50 gold from this, but most importantly, you can also win the map that O’Brian was bragging about earlier. He won’t just give up his prized map like that, though. You will have to put something valuable on the line as well. He will accept one of three different offers. First things first, you can offer to pay up 500 gold. Nice and simple, this might be the most practical option for some monetarily gifted pirates out there. The second option is to hand over Largo’s Black Pearl item if you are still hanging onto it. Finally, the third option is a monkey. No, that’s right; you can bet a monkey in your drinking game against O’Brian. The problem with this one is that you’re not likely to be able to get your hands on it during your first visit to Tacarigua, so you probably won’t be able to bet it. It’s best to lay one of the other options on the line.

With the bets made and the stakes set, it’s time for the drinking game. You will have to chug down booze as fast as you possibly can. Whoever can finish the most beer fastest will be crowned the winner. O’Brian will demand that you not just drink any old liquor, though. You will have to down the Painkiller alcohol, the most powerful and potent of all of the drinks in the tavern. Each bottle costs a whopping 150 gold. Go to the bar and purchase a Painkiller, and then head back to O’Brian and tell him that you are ready to take him on at his own game. You might want to save your game before you start the challenge in earnest, as that way you can simply reset if anything goes wrong and you lose something that you don’t want to let go of just yet.

The contest will play out as a minigame. When the challenge begins, you will enter a sort of first person perspective from which you will be able to see your hand and a big stack of bottles on the table. You will have to catch all of the bottles before chugging them down. There’s a certain strategy to catching the bottles, so take it slowly because you don’t want any of them to break. If you move too quickly, you can actually drop the bottle and break it, drunk as you all are by now. When the bottle is tossed, try to hit the neck of the bottle. Timing it that way will ensure that you have the longest window to actually catch the bottle, as the neck is right in the middle of the bottle’s hit box. After a while, your hand will begin to shake. After a few more, not only will your hand continue to shake, but it will start to react slower to your prompts as well. Be careful, but also be sure to finish all of your bottles before your opponent downs his. Barring a save restart, you won’t be able to restart this quest after you fail it. You may also lose whatever it is you put in, meaning you can potentially fail Largo’s quest line by losing this challenge as well.

If you win, though, the rewards will be great. You will get your hands on O’Brian’s treasure map as promised, thus completing the O’Brian’s Treasure Map quest and opening up the next quest, called O’Brian’s Treasure. You will also receive 50 Glory points for beating O’Brian at his own game.