When Jake notices Gina sneaking out of Captain Holt's office with a bag, he tells Terry and Amy that the Captain isn't wearing any pants. Jake put this together after seeing Holt enter his office with a hot bowl of soup, hearing Holt yell, and then seeing Gina enter Holt's office empty-handed before leaving with an opaque bag. Jake goes to Holt's office to try get proof of Holt's pantslessness. Jake wants the Captain to sign something at his desk, but he won't make. Then, Jake claims Yo-Yo Ma is in the precinct, but Holt knows his tour schedule. Finally, Jake enters with a hot bowl of soup of his own. Growing tired of Jake wasting his time, the Captain admits he is indeed without pants after a soup accident. Jake's celebration knocks over the hot soup on his own lap. Later, when Amy enters Holt's office, she finds both of them at his desk without pants.

Jake goes to the break room to tell the squad he's got the driving directions for their trip to Charles' beachhouse. The squad are excited for their detectives-only getaway - no spouses, no work, no bosses. Later, Gina finds Amy packing two bottles of vodka into her bag. Gina wonders whether this weekend she will finally meet six-drink Amy.

As the squad leave the precinct, Marcus approaches Rosa to say goodbye and give her a phone charger so they can stay in touch long-distance. Even though Rosa is uncomfortable with the public display of affection, she smiles when Marcus kisses her. Meanwhile, Jake goes to Captain Holt's office to hand in a closed case. After thanking Holt for giving them a half-day, Jake wonders about the sort of workplace shenanigans Holt got into back in the day. When Holt mentions he was excluded from most social gatherings as a gay, black detective, Jake feels bad for the captain.

As the squad gathers in living room of Boyle's beach house, Amy is ready to start the party with two shots. When Jake arrives, he ruins the mood by telling them Captain Holt's here. After Boyle shows the Captain to his room, the rest of the squad are angry at Jake for inviting Holt. Amy admits she is not comfortable being drunk around Holt, while Scully and Hitchcock are only interested in trying to sell him on their investment opportunity - a sunken casino ship off the coast of Delaware. Before lunch, Boyle finds Rosa in the basement texting Marcus. She asks for Boyle's help sending romantic texts.

At lunch, Holt wonders how the squad usually blow off steam. Jake mentions they usually just gossip about other colleagues. When the squad joke about another workmate, Captain Holt dampens the mood by remarking how he's a good cop and he likes him. Captain Holt leads a toast to the squad, encouraging Amy to have her third drink as Gina counts. After lunch, the Captain thinks it would be a good idea to go for a walk on the beach - even though it's the middle of winter. Jake tries to act like he's excited, but he's the only one trying. On the walk, only Holt enjoys the bracing cold wind. In an effort to keep warm, Amy downs a bottle of cognac - introducing the squad to four-drink Amy.

Back at the beach house, the squad relax in the hot tub. Captain Holt has them turn the jets off as they're too distracting. Afterwards, the squad smoke cigars. Captain Holt tells a story about his old partner who used to smoke cigars. Although the squad is initially interested in Holt's story, he breaks the mood by describing how the former partner died of multiple cancers.

When Jake goes down to the basement, he admits it sucks having Captain Holt here with them. When Vacation Terry mentions how he's happy with his own party going on, Jake has an idea to run two parallel parties - one boring one upstairs with Holt, and a fun one downstairs. At least three people must stay upstairs with the Captain at all times, and they'll split the work into twenty-minute shifts.

As Holt bores the upstairs party with the music of Joram Leifgrum, the flutist, the squad has fun downstairs. Before Amy goes upstairs for her shift, Gina gives her another drink. Five drink Amy is unusually confident. When she goes upstairs, she asks Holt for a raise. Jake doesn't think confident Amy is working out, so he gives her another drink - six drink Amy. When Scully and Hitchcock escape upstairs to talk to the captain about their casino investment, Jake distracts Scully with a sandwich.

When Jake returns downstairs, he complains about the others letting Scully and Hitchcock out of their sights. As the parties continue, downstairs Jake wonders how many people are left upstairs after he finds Amy and Terry both downstairs. Before Jake can send anybody else upstairs, the Captain comes down and is upset to find them having another party without him.

As the squad worry about Captain Holt's feelings, Jake leaves to try patch things up. When Rosa wants Charles's advice about Marcus's texts, he tells her it would be best for her to do it herself. Rosa admits she really likes Marcus and doesn't want to mess it up, so Boyle tells her to say that. When Marcus responds with a shirtless pic, Rosa leaves Boyle to text Marcus back. Meanwhile, Gina tries to help six-drink Amy, who it turns out is just sad. Gina gives her a drink of water, causing Amy to remark that Gina's her friend.

When Jake finds Captain Holt in the hot tub, it's the Captain who apologizes. He says he shouldn't have forgot that getaway is really for the detectives, and that one of the things they're getting away from is him. Jake mentions how they usually just get drunk and act like crazy idiots, but it's hard to do with the Captain around. Jake says perhaps instead of them trying to rise to the Captain's level, he should stoop down to theirs.

In the fun basement party, Jake introduces the squad to a new game, "Real Ray of Fake Ray?", where they must guess whether a phrase is something Captain Holt actually said or not. Jake introduces their special guest, Captain Holt, who is greeted enthusiastically by the squad, who enjoy the game with Holt.