With The Moustaches and Akbar's Players out ahead, Gay Angst and S.W.A.T. make the rappel without problems. Valley Girls are still waiting on Christina whose rope has gotten stuck. She gets it fixed, but not before they fall to last place. Really Limited are in third despite Ike being in a lot of pain. Erik says Ike will keep going until his toes fall off. The Moustaches arrive at the instruction at Lake Bin Waiting For Your Ass To Get Here. Teams must inflate two kayaks and paddle to Prison Island. Akbar's Players arrive as The Moustaches begin inflating. Yet again, we have to hear about Akbar's disdain for kayaks, but he's got a point that this time is worse because there will only be two kayaks for three people and he has enough trouble being one man on one kayak. His team decides it's best if he shares a kayak so that they have the power of two men paddling it. Good in theory, but Akbar eats it immediately as Robert tries to give the kayak a push start and it flips, throwing Akbar off the side. Most teams see this kayaking part of the stage as an opportunity to make a move for better position. AJ's barking out orders to Gay Angst in hopes they can move up. Jeff says that they have to view these areas as opportunities to capitalize on Ike not being on his feet. The teams are all making a go of it except for Akbar's Players who are struggling and fall to fifth place in front of The Valley Girls.
The Moustaches reach the instructions at Prison Island first and will be heading to Saddle Island from here. To get there, teams will transform their kayaks into one catamaran sail boat. There's a glimmer of gypsy failure hope here because Eric says he has no sailing skills. The S.W.A.T., Gay Angst and Really Limited arrive at the checkpoint in that order. Akbar's Players arrive and read that they will be building a catamaran. Akbarism in TH about the word "catamaran": "First off, what is that?" Akbar's not the only one confused. Jeff says all the instructions for building the catamaran were in sailing terms. Place the pole of the mast into the hole in the port side of the poop deck, etc. Because of the difficulty with the instructions, The Valley Girls are able to catch up to the rest of the teams, except for The Moustaches who are already setting sail for Saddle Island with a healthy lead. Gay Angst gets their catamaran built next, followed by Really Limited, S.W.A.T. and Akbar's Players. The Valley Girls have a little bit of trouble with building, but not much and figure their exemplary teamwork will get them back in the race. Natalie says Christina was like, "YEAH! It'll be just like wind surfing" and they were like, "Uh... OK," because I'm sure none of them have been wind surfing before. They're shown immediately having issues with keeping their sail up. The camera lingers on them for a minute in a high crane shot and then zooms to Team Gay Angst who are a bit ahead of them, but bickering and spinning around in their boat. Really Limited and S.W.A.T catch a bit of wind and start gaining on The Moustaches as Akbar's Players pass up Gay Angst who have let their troubles turn into in-fighting. It gets so bad Akbar says he could hear a huge commotion all the way at his boat as they were passing by. AJ and Ryan are really going at it, and AJ is totally bringing up water under the bridge. AJ: "When things get tough, just like you do in life, you freak the fuck out because you don't know how to deal with tough situations. You walk out. You are a quitter, Ryan." Impossible expeditions always bring out the worst in people.