- Arrive on the faraway island
- Stop the production of the mechanical pelicans.
How to Complete & Dialogue
Gameplay begins with Murray. Once he reaches the marker located near the gallows, a cutscene will start.
- Henriette: (Henriette jumps down from a rooftop in front of Murray.) Don't worry, mate. Bentley sent me to accompany you to the harbor.
- Murray: "The Murray" doesn't need help right now.
- Henriette: Well, actually, you do, mate. According to Bentley, there be many pirates that are trying to sink the H.M.S. Triumph, which be headed to the harbor even as we speak, and Carmelita is trying to fend them off.
- Murray: Uh-oh. Wait, what's that ship again?
- Henriette: That be the H.M.S. Triumph. It's commanded by one of me greatest rivals, Commodore Morgan Fox.
- Murray: Wait. Morgan Fox?! As in... Oh no!! Another of Carmelita's ancestor's is in danger?! Don't worry, Carmelita and Henriette, I'll save him! (Henriette and Murray run toward the harbor)
Murray must head toward the harbor within a specific amount of time and fight off the rooftop guards that have appeared there. This time limit is two minutes, and seeing how the harbor is far away from the gallows, Murray and Henriette must rely on the rooftops, seeing many flashlight guards appear on the route toward the harbor. Carmelita will be firing at the flashlight guards, so they won't be much of a concern. However, Murray and Henriette must combat the pirates within the time limit that is available to them, lest the H.M.S. Triumph won't make it to the harbor, as it wouldn't be safe to get too close. Once all of the pirates have been defeated, a cutscene will start.
- Sly: (Sly and Bentley reach Murray, Henriette and Carmelita.) Good. Everything is alright now. The ship is finally heading to the harbor.
- Bentley: Excellent!! Now, let's see if we can negotiate with the commodore regarding Black Beard. (The H.M.S. Triumph reaches the harbor. Sly and the gang get onto the ship to greet Commodore Morgan Fox. Instead, the commodore gets out of his ship with a blade at Henriette's throat.)
- Morgan: Pirates on my ship?! I'll have none of that kind of mischief aboard the Triumph!
- Henriette: Relax, Morgan. It be me, remember? (Henriette gives Morgan a sassy look, as if she were trying to woo him.)
- Morgan: (Morgan roles his eyes and sighs.) I remember you now, and I will not be falling for your tricks again. (Henriette looks slightly disappointed.) Henriette "One-Eye" Cooper, you are coming with me to the gallows. You and your new crew are.
- Henriette: Now hold up, mate! We be trying to get you to help us!
- Morgan: (Morgan has a shocked look on his face.) M-Me?! Helping pirates?! I-I would do nothing of the sort!
- Henriette: (Henriette turns to Sly.) He be ashamed of helping me crew out earlier last year with Salty Sam. (Henriette giggles mischievously.) Listen, mate. I be telling the truth when I tell you that we've been invaded by a monster.
- Morgan: Have you some proof?
- Henriette: Look at the flags, Morgan! Someone be messing with the island! (Morgan notices Penelope's symbol on some of the flags.)
- Morgan: It would appear that you told me the truth. Whose symbol is that and what manner of thing are we dealing with?
- Bentley: Um, excuse me, but we are dealing with a time-traveler, one we all once considered a friend. (Morgan looks at Bentley as if he was curious.)
- Morgan: What sort of contraption are you sitting on? It's quite interesting.
- Bentley: Let's not talk about my wheelchair right now, Morgan. (Morgan notices that not as many pirates are with Henriette.)
- Morgan: Is this all of your crew? What happened to the seagulls and that albatross?
- Henriette: (Henriette begins to feel slightly depressed.) Let's just say they be not as loyal as I thought.
- Sly: Yeah. Red Rum Roger and the rest of her crew work for Penelope now.
- Bentley: She's the time-traveler I mentioned, though it seems she's taken the identity of Black Beard now.
- Murray: (Murray sees a strange shape in the distance.) Guys! Look! It's another ship!
- Henriette: That's not just any ship, mates! That be my ship! That no-good rotten phantom is using my ship!! (Morgan looks through a spyglass in his pocket and sees Black Beard and Red Rum Roger.)
- Morgan: Everyone, get to your assigned stations now!! Load the cannons! We're sinking that ship once and for all!
- Carmelita: Wait, look! They're heading toward that island with the smoke. We should follow them instead.
- Sly: That Carmelita, always thinking of all the right plans.
- Bentley: Murray, you'll need to stay behind with me to help hold the fort! Carmelita and Henriette should be able to protect the Triumph when you reach the island. Now Sly, remember that costume that you wore in Blood Bath Bay?
- Sly: Yeah, what about it?
- Bentley: You'll need to wear it again. You'll need it if you're going to fool some of the pirates into thinking you're a new crew member. Oh and here's one of Roger's swords. Maybe Morgan will let you have a hand cannon, too. Now get going before Black Beard gets away! (Bentley and Murray get off of the boat as it leaves the harbor.)
After a loading screen begins and ends, a brief cutscene begins as the H.M.S. Triumph reaches the faraway island.
- Sly: (Sly puts on his Buccaneer Costume for the first time.) Okay. It's nice to know that Cantankerous Tim's clothes still fit. Henriette, can you, Morgan and Carmelita keep watch on the ship?
- Henriette: I be having the eyes of a hawk!
- Sly: Good. Now it's time to get this party started.
Sly's current location is far enough away from Black Beard's make him undetectable at the present moment. While in the Buccaneer Costume, enemies such as the Cutthroat Capuchins and Sinister Seagulls won't attack Sly, but Putrid Pelicans will. When Sly reaches a production facility, he'll need to rely on the pirates' inability to recognize him to get him past several enemies in the area. But before Sly can get into the facility, however, he must destroy seven Putrid Pelicans. The first is located by a treasure chest containing several wrenches and screwdrivers, which can be destroyed so Sly can gain a ton of coins. The second pelican is above the production facility on the roof. Be careful not to use the hand cannon, as it will attract attention from the other guards in the area, and make Sly fail the mission. Rather, Sly must climb up a vine leading to some rocks which act as stairs for Sly to walk up, allowing him to reach and defeat the pelican on the roof. The third pelican appears after the second one has been destroyed. Sly must simply jump down from the roof of the building, but not in front of the pelican. Then, Sly may use his saber to defeat the pelican in one blow. The fourth pelican is located near a small pool which has a generator in it. Sly just needs to get behind the pelican and slash it with his saber. The fifth, sixth, and seventh pelicans are all in one area, each close to one terminal. The sixth and seventh pelicans will never turn away from the terminal, while the fifth pelican will guard the other two. Sly must use his sword to defeat each guard in one slash. Once this is done, a cutscene will begin.
- Cutthroat Capuchin 1: (The capuchin monkey walks toward the facility with a fellow capuchin. He notices the destroyed pelicans.) By Black Beard's beard!! This be a terrible thing!
- Cutthroat Capuchin 2: Quick, matey! Try and get inside! We must warn the captain!!
- Sly: That's my cue. (Sly takes out a portable hacking device.) And here I thought I'd have Bentley hack the door's terminal. (Sly puts the portable hacking device in his pocket. Sly, while still in his Buccaneer Costume, manages to make it inside of the production facility's front entrance.)
- Cutthroat Capuchin 1: (The first capuchin notices Sly's presence.) Who be this landlubber behind us?
- Cutthroat Capuchin 2: (Both capuchins turn around.) Explain yourself, lad! Who are you??
- Sly: Relax, mates! I be a new recruit. I be Scurvy...uh...Will! Scurvy Will!
- Cutthroat Capuchin 1: Well, be on your guard, mate. There be a saboteur among us. We be going to alert Captain Black Beard of this. You go and watch over the...um...whatever it is that creates those pelicans.
- Cutthroat Capuchin 2: Good grief! I be wishing that we stuck with the raccoon girl now! (The capuchins both enter an elevator of some sort, and travel upward. Sly enters a room where many Putrid Pelicans are being built.)
- Sly: Oh wow. Those are a lot of pelicans. (Sly takes out his Binocucom.) Bentley, are you looking at this?
- Bentley: This doesn't look good, Sly! At this rate, even if we get rid of the robot production machines, there will still be too many guards and pirates to deal with!
- Sly: True, but my hand cannon should be able to blow up those machines.
- Bentley: Just be careful not to get caught on the way out, okay?
- Sly: I know, I know.
Sly must use his hand cannon to destroy all ten of the machines producing the pelican robots. But while this part is easy, it's the angry pelican robots that Sly will be forced to contend with that will be very difficult to handle. As soon as the first machine is destroyed, the guards will be on to Sly and a time limit will start. Sly must demolish the guard robots and machines within the time limit. Once this is done, one final cutscene will begin.
- Sly: Bentley, I've done it! The machines are completely destroyed!
- Bentley: Great! Now head to the ship immediately! Black Beard and Roger are probably on to you by now!
- Sly: Got it! (Sly heads out of the robot production room. He turns to his left and sees Black Beard.) Penelope! That suit is huge!
- Black Beard: It's certainly larger than your brain if you think you'll leave here alive, Cooper. (Sly dodges Black Beard's sword and manages to escape the production facility. Black Beard looks into the robot production room.) COOPER!!! I'LL KILL YOU FOR THIS!!!