Breakroom: Dwight stares into the snack machine and accuses Jim of putting his stuff in there since he's friends with the vending machine guy. We see a pencil cup, Dwight's name plate, and an assortment of Dwight office swag in the chip machine. Jim tells him a dollar for a stapler is pretty good and Pam decides she wants the pencil cup and goes ahead and buys it. Dwight protests and looks for his wallet to buy it from Pam, and Jim points at the machine and tell him it's at J1, but he's penniless without his wallet. Jim, helpful as always, hands Dwight a baggie full of nickels.
Michael heads into work and the staff looks at him expectantly, Phyllis asking where they are going this afternoon. In an interview, Jim and Pam talk about Michael's "mysterious memo" in which the staff was asked to pack for their first quarter camaraderie event and bring a toothbrush, a swimsuit, rubber soled shoes (as Jim says rubber soled shoes, the camera cuts to Kevin mischievously packing a strip of condoms) and a ski mask. "So that he can have us rob a bank and escape through the sewers," Jim explains. "And brush our teeth," Pam adds, laughing.
Stanley enters Michael's office and asks if its going to be an overnight trip, while Michael continues to chant "Stanley, Stanley, bo banley" and says the suspense is killing him. Michael finally relents and tells Stanley that they are going on a cruise on Lake Wallenpaupack. "In January?" Stanley asks. "It's cheaper," Michael replies. Michael interviews that it's not just another party but a leadership training exercise, and a mind-blowing experience.
In the conference room, Michael reveals their final destination and everyone is nonplussed except for Dwight, who pumps his fist excitedly. When Michael reveals it's a booze cruise, Meredith also seems happy. Ryan asks if he can skip it because he has a business school exam, but Michael refuses and tells him the cruise will turn his life around. Ryan says he's already in business school. Kelly asks why they were told to bring a bathing suit and Michael replies that it was to throw them off the scent of the cruise. When Kelly says she bought a bathing suit and took the tags off, Michael says the company can't pay for it. Michael introduces Brenda from corporate and then interviews that he is a great motivational speaker and he attended a Tony Robbins event at the airport (not the real course, you have to pay for that) and he incorporated a lot of his ideas into his own course.
"Leadership. The word ship is hidden inside leadership, as its derivation. So, if this office is in fact a ship, as its leader, I am the captain," Michael notes, putting on a captain's hat. "But we're all in the same boat. Teamwork!" Oscar interviews that last year, Michael's theme was "Bowl over the competition" and asks us to guess where they went. Michael asks everyone what the sales department is on the "ship that is the office." Darryl says that the sales department could be the sails. "Yes, Darryl," Michael replies condescendingly. "The sales department makes sales. Good." Michael says he sees them as the furnace and Jim asks how old this ship is. Michael helpfully explains that they are shoveling coal into the furnace like in "Titanic." Pam asks if he got the movie right and perhaps he means "The Hunt for Red October." In an interview, Jim bets his paycheck that Michael will stand in the front of the boat and yell "I'm king of the world!" during the first hour. Phyllis says that everyone in the engine room drowned, and Michael replies "Thank you, spoiler alert!" Increasingly frustrated, Michael tries to explain that they're happy in the furnace room, all dirty and grimy and singing their "ethnic songs." Michael changes his mind and says it might be warehouse, much to Darryl's astonishment. Michael says they'll continue on the ship.
Booze Cruise. Michael is singing the theme from "Gilligan's Island" and starts handing out characters. Pam is Marianne, Jim is the Professor, Katy is Ginger, Angela is Mrs. Howell, Kelly is a native, and Stanley is a Harlem Globetrotter. Michael dubs himself the Skipper and calls Dwight Gilligan. Captain Jack says he's the Skipper, but Michael can be Gilligan. Michael says he'd rather die. Captain Jack quickly pulls rank, and Michael interviews that manager is higher than captain, but on a boat, who knows, "it's nebu-los." Jim already wins his bet as Michael yells "I'm king of the world!"
Later, Michael is interrupting Captain Jack's welcome speech, much to his chagrin, but Dwight is already entranced by Captain Jack. Captain Jack tells everybody he's their party captain, and Michael shouts that he's their party captain too. Captain Jack is pissed and tells Michael to sit down.
Jim, Katy, Pam and Roy are at a table that Katy dubs the cool table. Roy laughs and Katy asks if Pam was a cheerleader. Roy says she was "Miss Artsy Fartsy" with the turtleneck and everything. Katy laughs and says that's hilarious, but Jim disagrees. Roy asks where Katy went to high school and when Katy says Bishop O'Hara, Roy replies "Hey slob, who care-za? We played you!" and recognizes her as cheering for them. Katy starts cheering and Jim and Pam make eye contact, while Pam does a little mock cheering shimmy.
Michael starts talking about life preservers and calls IT Support an important one, but Captain Jack interrupts and says it's time for the limbo contest. Captain Jack asks for a volunteer to hold his stick, and both Meredith and Dwight volunteer, but Dwight is more enthusiastic about it. Captain Jack tells Dwight it's usually a woman, but Dwight replies that he's stronger. Captain Jack asks Dwight if he'd like to steer the ship, and Dwight is awestruck. Dwight interviews that he was the youngest pilot in Pan-Am history: when he was four, he went into the cockpit and flew the plane and he was great at it and would have landed the plane if his dad didn't want to go back to their seats.
Captain Jack announces that it's time for the dance contest, but Michael insists that he be allowed to give his presentation. When Captain Jack doesn't budge, Michael dubs it a "motivational dance contest." He starts dancing spastically and calls it a "primal art form used in ancient times to express yourself with the body. And communicate!" Michael interviews that you have to take a break sometimes from being kind of boss who's always trying to teach people things and just be the boss of dancing. More footage of spastic dancing and idiotic moves.
Dwight is still steering and singing Irish dirges, but we see that someone else is steering the ship from above. Angela asks him to come inside, but Dwight insists that he needs to steer, much to Angela's frustration. Katy and Darryl are cheering Roy on as he does a "snorkel shot," while Pam looks on bemused and declines to do one. Pam asks Roy to go someplace quieter, but a drunk Roy says he needs to watch Darryl do his snorkel shot.
Jim and Pam go out onto the deck. "Sometimes I just don't get Roy," Pam confesses. Jim looks around nervously and Pam makes eye contact and says, "I mean, I don't know." They stare at each other for about ten seconds until Pam teases Jim and asks him what it's like dating a cheerleader. Jim laughs, but clearly doesn't want to ruin this moment with Pam with jokes and continues to look into her eyes in silence for ten more seconds, and clearly seems like he wants to say something. Pam, perhaps sensing that something might be up, tells Jim that she's cold and walks away, while Jim stares off into the dark lake, his body language suggesting that he's been defeated.
Captain Jack asks Michael what his presentation is about and Michael says it's about priorities and making decisions using the boat as an analogy and what is saved when it is sinking. While Captain Jack says women and children, Michael replies that it's salesman and profit-senders. Captain Jack calls it a stupid analogy and Michael accuses him of not knowing anything about leadership. Captain Jack says he was the captain of a coastal patrol boat during Desert Storm and Dwight is properly impressed and appears to take Captain Jack's side.
Back at the "cool table," Katy tells Pam that she'd like to be engaged, but Pam notes that she's been engaged for three years with no end in sight, so she shouldn't take her advice. Over at the bar, Captain Jack asks Jim who he would save if the office building was on fire. He looks to Pam, but says "The customer, because the customer is king." Captain Jack says he's sucking up. Roy staggers over and asks Captain Jack if he almost died while he was in the Navy. Jim walks away while Captain Jack says that he did and that he wasn't thinking about a customer, but his first wife, and that when he got home, he married her. Roy seems as though he's having a moment of (drunken) clarity while Jim tells the camera that he'd save the receptionist as he walks toward Pam and Katy.
Roy grabs the microphone and announces that enough is enough and sets the date of June 10th for their wedding. Pam is excited and is hugged by Katy and applauded as she walks over to Roy with tears in her eyes. They kiss while Jim looks crestfallen. Michael asks Roy if he motivated him to make the move, but Roy answers that it was Captain Jack. Captain Jack calls for celebration and notes that he can marry them right there as captain of the ship and Michael offers to marry them as regional manager of Dunder-Mifflin. Pam declines, noting that she wants her parents there. Michael says he can give her away, and again Pam declines.
Slow dancing music. Creed and Phyllis are dancing as are Pam and Roy. Katy and Jim look on from the deck window and Katy asks if he thinks they'll ever be like Pam and Roy. Jim quickly replies no, which upsets Katy. Katy asks why he even brought her there and Jim says he doesn't know and says they should break up. Captain Jack takes a giggling Meredith into the steering room of the boat. Michael is seasick and Dwight notes that Captain Jack told him he should look at the moon. "Captain Jack is a fart face!" Michael exclaims, vomiting into a paper bag. When Brenda looks concerned, Michael says he's on medication … Vomicillin.
Michael dismisses the band and continues with his speech. He tells everyone that the ship is sinking. Kevin, in his ski mask, shares a knowing look with Angela. All the passengers not from Dunder-Mifflin start to panic and some start passing out life preservers. Michael continues on with his business scenario as Angela and Kevin try to calm everyone down. But one guy jumps out the window of the boat. Captain Jack comes out with Meredith (topless, but covered by a life preserver) and asks what's going on.
Cut to an interview of Michael with his hands bound with garbage ties "in the brig." He says that if the guy jumping overboard had just waited he would be motivated instead of wet. Back in the boat, Katy is upset and looks like she's going to cry while other Dunder-Mifflin employees are asleep. Jim senses the awkwardness and joins Michael. Michael tells Jim that Captain Jack has a problem with authority and Jim reminds him that he told everyone the boat was sinking, but Michael insists that he caused the panic. "What a night," Jim sighs. Michael says he should be happy because his friend got engaged. Jim says she was already engaged, but Michael says that Roy told him the first one didn't count. Jim confesses that he "used to have a big thing for Pam," and Michael is incredulous and surprised, and reminds Jim that he made out with Jan. "Well Pam is cute," Michael says. "Yeah, she's really funny and she's warm and she just … I don't know," a tortured Jim sighs. Michael tells him not to give up, but Jim reminds him that she's engaged. "Psh. BFD. Engaged ain't married," Michael replies. "Never ever ever give up." Jim seems a little happier and daresay motivated now.
From the bottom deck, Dwight yells, "Don't worry, Michael, I'm taking us to shore!" Michael shakes his head and yells back, "It's a fake wheel, dummy!"