Oscar THs about last year's theme, "Bowl Over The Competition," and leaves it to us to guess where they went. Roller-skating?
Michael asks what part of the ship sales would be. Misunderstanding and then disregarding Darryl's guess that sales is the sails, Michael calls them the furnace. The furnace? "How old is this ship?" Jim wonders. Michael wants to move on to the movie Titanic, which Jim and Pam amusingly pretend to never have heard of. Jim THs, "Michael stands in front of the boat and says the he's king of the world in the first hour or I give you my next paycheck." Back in the conference room, Michael keeps going on about the engine room guys, "sweaty and grimy and singing their ethnic songs," which makes him reconsider that maybe the engine room is actually the warehouse. Darryl begins to take offense, and Brenda Something starts writing on her pad as Michael, realizing his little presentation is headed for the reef, says they'll talk about it on the boat.
As the DM crew board the boat on what looks like a very chilly evening, Michael tries to pump everyone up by singing the Gilligan's Island theme and assigning everyone roles: Pam's Mary Ann, Jim and his then-girlfriend Katy are the Professor and Ginger (respectively), Angela's Mrs. Howell, Kelly's a "native," Stanley's one of the Globetrotters, Michael himself is the Skipper, and Dwight is Gilligan. Except then, the boat's actual captain turns up, introducing himself as Captain Jack. Not that he's anything like the Captain Jack you're thinking of. Or that other one, for that matter. Captain Jack politely but firmly says he's the skipper of the boat, and of anyone who steps aboard it. Michael THs cluelessly about where a regional manager falls in the chain of command on a boat versus an office, and is then seen doing the "king of the world" thing before the boat's even clear of the dock. Jim grins at us, pointing at his watch. I'm not giving you my paycheck, Halpert.
Now that the cruise is underway, everyone is in the reception-hall-looking space belowdecks, Captain Jack gets everyone's attention to try to do the safety briefing. Except that he has to share the floor with Michael, also wearing his own captain's hat. Captain Jack says he's also the "party captain," and Michael says he is too. He tries to take over, until Captain Jack points out that there are other passengers besides the ones from Dunder Mifflin on the boat. Captain Jack needs to back up a bit; Michael is still struggling with the concept of other people besides Michael being on the planet.