The last great “Housewives” trip: “Scary Island” and the end of RHONY’s Golden Age

If you Googled the words “‘Housewives’ trip” 15 years ago, the search results were probably more likely to return a sketchy link to some fetish site depicting clumsy homemakers, rather than a wealth of Reddit threads where users fight about reality television. (Now all that obscure fetish content has moved to TikTok, anyway.) These days, “‘Housewives’ trip” is synonymous with the most outlandish, uncouth, highly compelling television that the reality genre has to offer. In a “Real Housewives” franchise, cast trips are something that loyal viewers anticipate all season long. Bravo producers ship a handful of women off to some exotic locale — and, sometimes, Montana is a Housewife’s definition of exotic — where cameras film them morning, noon and night. When all of the Housewives are in one place, no one can get away with anything. Tensions run high, and if all goes according to plan for Bravo, ratings run even higher.

Now a staple of the long-running franchise, a “Housewives” trip wasn’t always a given. In its early years, Bravo’s relatively modest success meant that the network likely didn’t have the cash to foot such a lavish getaway. Maybe “Real Housewives of Orange County” would take a day trip to Lake Havasu, where Vicki Gunvalson would be hit in the head with a football so hard that it would make her fall for a cancer-faking Casanova years later, but that was the extent of their travels. And leaving the mainland United States was unheard of, that is, until the cast of “Real Housewives of New York” Season 3 took a once-in-a-lifetime, unforgettable trip to St. John, one of the U.S. Virgin Islands. Across three explosive, landmark episodes, the St. John excursion turned into a franchise-altering nightmare for the women insulated on their little archipelago, hauntingly dubbed “Scary Island” by cast member Kelly Bensimon. The three-episode arc has become the subject of study for superfans and Bravo historians alike. It didn’t just change the “Real Housewives” format; it altered expectations for viewers around the world, raising the bar so high that “Real Housewives of New York” would inevitably come crashing down.

Now, 15 long years after the “Scary Island” trip aired, “RHONY” has gone dark. When a spate of new and returning Bravo shows were announced in early May, “RHONY” — which was rebooted from its original state in 2023 — was nowhere to be found. Over the following days, Bravo factotum Andy Cohen assured fans that the show wasn’t going anywhere. But after the reboot crashed and burned so epically, it seems as though Bravo execs may be looking to retool the franchise once more to try to capture its glory days, something Matías Franco, a “Housewives” archivist responsible for some of the most beloved “RHONY” fancams, isn’t sure will be possible.

“Social media has changed the franchise as a whole, and unfortunately, it’s difficult to see ‘Housewives’ ever being the way it was,” Franco says. “Knowing your every action will be scrutinized and people will be giving you immediate feedback in your comments has to alter the way you behave in front of the cameras.” 

Kelly Killoren Bensimon and Sonja Morgan (Courtesy of Bravo)Nowadays, there are countless blogs monitoring and ripping apart “Real Housewives” behavior on the daily, and cast members face relentless scrutiny and hate every time they post on social media. However, when the Season 3 cast trip aired in May 2010, Twitter was still an archaic SMS service. Instagram hadn’t even hit the app store. Websites needed to be coded by a professional. It was a completely different time to be a reality TV star, one where a Real Housewife’s bad behavior would earn a slap on the wrist from Bravo producers, and not persistent death threats. 

“[Housewives] felt safe from seeing what people were saying,” says Carey O’Donnell, a writer and podcaster who has been covering the reality television sphere on Sexy Unique Podcast with his co-host Lara Marie Schoenhals for over half a decade. “They were insulated. We got to see people being so candid and ridiculous because they weren’t self-editing. I almost feel a little bad for the news girls because it’s a tall order. These are big shoes to fill. They’re coming in a time when TV is dictated by what people are saying on Twitter.” 

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Had social media been as prevalent when the “Scary Island” trip first aired, there wouldn’t be one Housewife on the trip who could’ve escaped the lethal criticisms of Bravo fanatics. As soon as they landed in St. John, it was as if each cast member got sunstroke and proceeded to spend the next few days going in and out of paranoia, fear and delusion. Ramona Singer was frenzied and drinking like a fish. Sonja Morgan was reeling from a divorce and trying to hold herself and everyone else together. A pregnant Bethenny Frankel was grieving her estranged, recently deceased father and swatting away insults left and right. The sight of Jill Zarin appearing out of the blue on the final day of the trip caused Alex McCord to physically shake in fear. And, most notably, Kelly Bensimon rounded out three days of tension between her and Frankel with a full-fledged, rambling breakdown, where subjects skittered between everything from Gwyneth Paltrow and gummy bears to Al Sharpton’s hairstyle. 

Bensimon’s incoherent chatter remains one of the series’ darkest moments, punctuated by Frankel throwing her hands into the air, screaming at Bensimon to go to sleep. But O’Donnell likens the dynamics of the cast at that time to a dysfunctional sisterhood, adding that Morgan defusing the situation with Bensimon felt like someone trying to comfort a sibling. “That’s why ‘RHONY’ was different,” O’Donnell says. “Bethenny and Kelly were such yin and yang. They were astral opposites. But at the end of the day, there was a strange love and respect for each other despite Kelly being Bethenny’s main foil. At that time, Kelly had the upper hand in her placement in society. And when she came into Bethenny’s orbit, Bethenny was still the underdog. And I think Kelly did shake Bethenny, because Kelly was in that upper echelon [of New York society] at that time.”

Sonja Morgan (Courtesy of Bravo). Bensimon had also spent the better part of the trip taking shots at Frankel, saying that Frankel was a “cook, not a chef” and that Frankel being on the trip so soon after her father’s passing was “creepy.” But Frankel has always been a quick wit, her silver tongue making her a formidable match for any of her opponents during her time on “RHONY.” The tension between the two women had been mounting since the previous season, when they met at a New York bar to hash out their differences. During that fight, Frankel learned that letting Bensimon talk herself in circles was her greatest stealth weapon when going toe-to-toe with her enemy. Bensimon ended  Season 2 looking self-centered and detached, while Frankel was calm and collected.

Undoubtedly, Bensimon noted the way she came off in the final edit. When she returned for Season 3, she was slightly more magnanimous and less flighty, trying her best to achieve harmony with the rest of the cast. But Frankel was always ready to give Bensimon her unfiltered thoughts. The two managed to avoid each other for most of Season 3, until the cast trip put them under one roof with nowhere else to go. 

Because Frankel was so ready to check her opponent — whether it be about the difference between chefs and cooks, or Bensimon’s peculiar idea that a one-night-stand was the equivalent of having risky unprotected sex — it’s no surprise Bensimon quickly felt defeated. And when the group migrated from a yacht to a lavish house on St. John, where Frankel placed monogrammed gift bags outside of all of their doors, it was the last straw for Bensimon, who tossed herself onto a bed crying before placing a phone call that would change “Real Housewives” forever. “I’m alone on Scary Island with no friends,” Bensimon told her castmate Luann de Lesseps over the phone. (De Lesseps could not make it on the trip because she was busy recording her debut dance single.)

“Kelly’s behavior is one of the most interesting topics to discuss because it’s still a mystery to this day,” Franco says, recalling Bensimon’s assertion that Frankel was trying to kill her. “Did she actually have a psychotic break? Were there outside stressors we weren’t privy to? So many questions are unanswered, which makes it such a juicy topic to speculate about … Looking back, there’s a clear lack of empathy for Kelly’s mental state. How her pent-up frustrations toward Bethenny evolved into nightmares of being stabbed in her sleep, we may never know, but that’s why it’s so fascinating to think about.” (For her part, Bensimon posted a meandering, 24-minute long “explanation” about the episodes a few years back that offers very little insight into what really happened.)

Bethenny Frankel is seen outside ABC Studio on July 20, 2023 in New York City. (Raymond Hall/GC Images/Getty Images)

Fans lapped the chaos up. The episodes broke “RHONY” ratings records, achieving an all-time high for the show up to that point. Forum commenters chimed in too, saying it was “both the funniest and scariest episode to date” and that the long-teased episode “did not disappoint.” The Scary Island cast trip quickly became the benchmark for all future “Housewives” vacations. If a certain city’s cast couldn’t match the drama that the women of New York turned out over a few days of sunny psychosis, watching the trip was considered a waste of time. Even “RHONY” couldn’t live up to its one-two punch of Scary Island and the following season’s trip to Morocco. There were meme-able moments aplenty, sure. But none had the kind of gripping, real-life ramifications of St. John. And in the contemporary era of “Real Housewives,” creating an atmosphere where the cast isn’t hyper-aware of how they’re coming across to the viewer prevents most recent cast trips from being memorable after they’re over.

With all the hand-wringing from Cohen, Bravo and fans about the future of “RHONY,” it seems unlikely that the show will ever find stable enough footing to create a trip as infamous as Scary Island. The show is too far removed from its glory days, and Housewives are too tempted to soften their behavior, lest they face the ire of Bravo fans sitting at the edge of their seats, waiting for any reason to publicly call for someone’s removal from the show. The idea of anyone taking to YouTube to post a PSA calling out systematic bullying, as Bensimon did after the Scary Island episodes aired, is unfathomable. Today, the cast would be tight-lipped until word about their fate came down from Cohen and the Bravo gods. 

“The ‘RHONY’ heyday might be gone forever,” O’Donnell says. “We should be happy with what we have. I’m rewatching right now, and I just don’t think it’s possible to recreate that, even if we have some of the [original cast members] mixed in.”

“I hate to sound so depressing,” he adds. “But we have to just love what we had, when we had it, and accept that things will never be the same. For us viewers, it was Camelot.”