A Plot: Pop-Pop (Murray's father) surprises the family with an ill-advised winter cruise to Canada.
B Plot: Erica stirs up holiday trouble at home.
- Casanova Wannabe: Barry deals with his current lack of a girlfriend by asking elderly passengers if they have hot grandchildren, and flirting with Jenny, the cruise ship's director.
- Didn't Think This Through: The Tag ends with Barry throwing his useless bowling ball into one of Adam's trash bags, with the others too late to stop him before the heavy ball forces the bag down and breaks a table.
- Exact Words: The family initially think that Pop-Pop got them a luxury cruise to the Caribbean, specifically the island of Saint John. But it turns out that, when he said the cruise went to St. John's, he meant the Canadian city.
- Feeling Their Age: Pop-Pop eventually reveals that his main motivation for the whole cruise and reconnecting with Murray was him starting to feel the pains of old age, and being afraid that he couldn't afford a nurse to take care of him.
- Foolish Sibling, Responsible Sibling: Geoff's parents eventually admit that they've always seen him as the responsible one, and apologize for being overly harsh about minor slights while giving his sister Joanne so much freedom that she's mismanaging her own life.
- Gift of Song: Joanne announces her plans to drop out of college and become a singer, and punctuates this point by performing Elton John's "Your Song" - badly - for her parents as her Hanukkah present.
- Gone Horribly Wrong: Erica decides to spend the holidays with Geoff because she assumes it'll be much less chaotic than being stuck on a ship with her family...and then Geoff's sister comes home from law school, causing a different kind of chaos.
- Hanukkah Episode: As the title implies, the episode features the Goldbergs celebrating Hanukkah. Pop-Pop's cruise is initially presented as a Hanukkah gift, and Erica celebrates the holiday with the Schwartz family.
- Mistaken for Romance: Jenny seems to pay much more attention to Adam than to Barry...because she thinks Adam is a child that isn't aware of events more appropriate for younger age groups than the bingo and shuffleboard games she spots him at.
- Motivational Lie: After Adam learns why Jenny was paying more attention to him, he tells Barry that Jenny was using him to get to Barry, so Barry's confidence in himself gets the boost it needs.
- My New Gift Is Lame: Aside from Pop-Pop's cruise that he couldn't pay for, The Tag features Barry, Erica, and Adam receiving a bowling ball without holes, a used shower cap, and a box of trash bags from him, respectively.
- Once Done, Never Forgotten: Geoff's family never lets him forget about his past mistakes, like when he was nine and dropped a match lighting Hanukkah candles.
- Parental Favoritism: Geoff's parents clearly appear to be more proud that their daughter Joanne is going to be a lawyer than Geoff becoming an orthodontist...even though Geoff's father is an orthodontist. Even when she announces dropping out to be a musician despite having no musical skills, they show nothing but support. However, they eventually admit that the reason they praise Joanne so much is because they thought she'd be a mess without it, and that they'll be more strict with Joanne in the future (starting by forcing her to go back to law school).
- Rage Breaking Point: When Geoff's sister's Hanukkah gift for everyone is singing a song off-key that moves his parents to tears, when Geoff had spent months painting a family portrait (which just has his father comment that he could've spent his free time studying), Geoff finally calls out his parents for their Parental Favoritism. He also gets Erica to out-perform his sister with just her natural talent, for good measure.
- The Scrooge: Pop-Pop's gift of a cruise isn't as generous as it seems, considering that the family originally thought he was treating them to a trip to the Caribbean instead of Canada. He later reveals he needs Beverly to actually pay for the entire cruise in addition to settling some of his personal debts.
- The Unfavorite: Geoff feels like one as his parents dote on Joanne, even though she is clearly not as responsible and talented as they say she is. The parents then confess to Geoff that while they're sure he'll go on to be successful without their help, Joanne needs all the support she can get.
- Was It All a Lie?: Murray has this reaction when he learns that Pop-Pop was insincere about gifting the family a cruise. Pop-Pop admits that he did want to get closer to his son before he grew too old to take care of himself, but felt he had to rely on trickery because of their past relationship problems.
- Wintry Auroral Sky: One caps off the episode, with Murray and Pop-Pop enjoying the view after reconciling, soon after joined by the rest of the family.
