It’s Thanksgiving in Canada. What better time to meditate on the thing in the world I’m most thankful for: Real Housewives of New York City cast trips. Since Housewives and listicles go together like turkey and cranberry sauce, here’s a ranking.
As with any ranking, pedagogy is of the utmost importance, so we’ll start by defining a “cast trip.” For our purposes, we’re talking about the main vacation attended by the entire cast (as opposed to mini-jaunts like season nine’s ski trip to Vermont). We’re also excluding trips to the Berkshires, which constitute their own beloved, essential genre. In brief: we’ll be ranking Scary Island (season three), Morocco (season four), St. Barth’s (season five), Montana (season six), Turks and Caicos (season seven), Miami (season eight) and Mexico (season nine).
One last caveat before we dive in: RHONY cast trips are the gold standard of Real Housewives content. I would happily have any of these episodes played on loop at my wake. I’m choosing favourites amongst my children here. I hope you respect the sacrifice I’m making for you.
7. Montana (Season 6)
Much as season six is the weak link among RHONY seasons, so too is Montana handily the least amazing cast trip. But this is only by comparison to a crowded galaxy of stars; on its own merits, Montana is a perfectly fine suite of episodes. There’s some hilarious sorority girl drama between Heather and Kristen, and LuAnn lays into Sonja over her dalliances with the undisputed best member of Team Sonja, Satoko the gossipy facialist. But the best drama is between Aviva and the producers, as Aviva bails on the trip on account of asthma or tuberculosis or diabetes or something and gets cut from the main credits for her troubles.
6. Miami (Season 8)
It feels absurd that Miami, the climactic shit show of one of the most amazing Housewives seasons ever, should be this low, but that is the calibre of the competition. To be clear, I recommend Miami to literally anyone. Bethenny’s photos of Tom’s infidelity hang like an anvil over the entire trip before finally dropping in one of the best sustained action scenes in the history of the show. “It’s about Tom” is a masterpiece of big-D Drama, serving both as the most important scene in the whirlwind saga of LuAnn and Tom, and the distillation of a decade of angst between Bethenny and LuAnn (reminder: the Berkshires massacre happened only ten episodes before this).
5. Morocco (Season 4)
This trip is the last hurrah for the O.G. cast, all of whom are on their best (read: most absurd) behaviour. Sonja arrives fresh off the reveal of the financial ruin that will hound her for the next five years. Ramona and Jill come to the tearful end of their friendship, which was historically very tight and never a barely civil minefield of passive-aggression. Alex emerges from her cabinet in her Herman Munster shoes to assail LuAnn and ruin Kelly’s henna tattoo. And we learn of the mysterious existence of une autre femme. Perhaps best of all, Morocco marks the exact point that the producers formally cut their losses on Cindy Barshop and just started editing her out of the show, after which the season flies.
4. Turks and Caicos (Season 7)
Turks and Caicos packs an impressive amount of drama into its three-and-a-half-episode run: Ramona and Bethenny go through the motions of Rapology #24207B, Sonja spirals into a bout of delusion so bad they name the episode after her, Dorinda indulges in her first drunken attempt on another Housewife’s life (a baffled Heather Thomson, always the unwitting victim of these chicks’ stray bullets), and LuAnn’s attempts to catch some dick abroad land her in hot water yet again. It’s alright, though; the Countess always keeps her cool. Perfect to view with a plate of eggs à la française and a hefty hangover.
3. Mexico (Season 9)
Something of an oddity among its peer group, Mexico is more notable for its lack of fighting than any specific argument. That’s not to say that it’s totally drama-free: Ramona is her typical banshee self about room assignments, Sonja has never been more horrible to Tinsley, and Dorinda predictably crosses over into The Dark Place with Bethenny after a few too many drinks. But really, Mexico is best watched for the lighthearted spectacle of seven of television’s most endearing and eccentric alcoholics getting blind hammered on tequila and pratfalling into bushes, engaging in tear-drenched apologies, drawing their own blood while drunkenly fucking with knives, etc.
2. St. Barth’s (Season 5)
St. Barth’s is a splendid disaster with nearly every cast member at their full glory. The saga of Thomas the pirate is maybe the best stretch of non-D’Agostino material in the LuAnn canon (LuAnnon?). Aviva arrives in fittingly melodramatic style and promptly gets eviscerated by Ramonja at the height of their drunken terror. And there’s a real joy to watching audience proxy Carole in her debut season, slowly losing her mind as she comes to grips with her new job description.
1. Scary Island (Season 3)
Yes, yes, I know. Quelle surprise. Were I a true edgelord, I’d make some case for Montana as the best trip and blow your minds. But Scary Island is widely regarded as the Citizen Kane of Real Housewives (the episode with Kelly’s iconic meltdown is probably the consensus Best Episode Ever) and I don’t disagree. I often reference psychological thrillers when waxing Housewifery, but I’ve never seen a more effective thriller than this. The slow build-up from annoyance to dread to confusion to alarm to terror as Kelly unspools herself over two episodes is unlike anything I’d watched before or since, and the end sting of Jill Zarin arriving on the terrace is for all the world like the undead killer’s hand lurching out of the grave. There’s a reason no one remembers the actual geographic name of Scary Island. It’s a place from an Agatha Christie novel, a bespoke remote nightmare born from a twisted imagination to be the site of atrocities.