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.
Replay of AJ's tirade on Ryan. AJ talks about times in their relationship when Ryan would literally just walk out on him. He says it's frustrating because he loves Ryan and Kari so much he would never walk out on them. Back on the catamaran, Kari tells AJ to just shut up. It's a stark contrast to The Valley Girls who are sort of giggling at their misfortune. Brittany does start blaming Christina for saying they'd know what to do, but they resign themselves to basically paddling the whole way without help from the sail. And that ends up being the case for The Moustaches, too, who find themselves out in front, but stalled out with no wind. Really Limited and S.W.A.T. fortuitously catch some wind at that exact moment and also decide to paddle like crazy to try and pass The Moustaches, so they end up in a sort of three-way race in which The Moustaches are caught off guard. It turns into a two-way race between S.W.A.T. and Really Limited. Jeff says he realized at that point it would be a foot race once they got off the boat. He starts yelling at Ike to get ready to jump off the catamaran onto his good foot to get a head start on the run. Amazingly, Ike reaches the overnight camp first and Really Limited beats The S.W.A.T. there. It's such an exciting finish for the day, Salmoni actually sounds excited when he tells Really Limited they've earned the three-minute head start in the morning. S.W.A.T. take second, Moustaches third, Akbar's Players fourth, Gay Angst fifth. AJ musters enough good spirit after the disaster on the boat to quip, "I like sailors," but sailing not so much. The Valley Girls are in last place, but are still all smiles. Salmoni needlessly reminds them if they come in last place tomorrow, they won't be smiling.