It’s finally that time of year again: when the days feel warmer and the nights get longer, and Bravo premieres yet another promising season of the Real Housewives of New York. Although we’re only two episodes deep, season 13 of RHONY has already served the fans some long-due belly laughs, Sonja’s typical townhouse antics, and a Hamptons party filled with high-pitched screams, interpretive dancing, and Swarovski pasties. Considering Bravo’s first attempt at an All-Star iteration will be presented this Fall as an eight-day vacation to Turks & Caicos, it’s safe to assume the sand-filled trips and weekend getaways are a staple to the Real Housewives brand.
This week, RHONY‘s season 13 housewives returned to The Hamptons to throw a Burning Man-themed party in Ramona’s backyard, tiring out newcomer Eboni K. Williams, who happens to be the youngest of the bunch! Despite their differences, the ladies of New York have always delivered the most iconic and outrageous vacations across the franchise. Here’s our definitive breakdown of the top ten most iconic RHONY vacations.
10. The Hamptons, Season 12
The Hamptons have been a mainstay on RHONY since its conception, but the audience had never seen a Hamptons trip quite like season 12’s rager. Despite being fresh meat, Married to the Mob founder and outspoken rebel Leah McSweeney surely cemented her place in Real Housewives history as she tore apart Ramona’s picturesque McMansion, pummeling lit tiki torches butt naked across Ramona’s yard. Leah’s lashing out wasn’t fully in vain as she was condemning the 2017 Charlottesville protests where white supremacists marched with tiki torches to chant abominations such as “you will not replace us.”
She also convinced a bashful Tinsley Mortimer and couldn’t-be-asked-soon-enough Sonja Morgan to join her in a skinny dipping session, which resulted in the photo above, a true Housewives masterpiece. A disgruntled Ramona uncovered quite the mess amidst the morning’s hangovers and harsh lighting, finding an empty champagne bottle floating in the pool and a random vibrator in a leftover chicken dish? Fans quickly fawned over RHONY‘s new woke Queen, who showed the OG the women they had finally met their match!
9. The Berkshires, Season 8
Similar to The Hamptons, The Berkshires quickly became a tradition on RHONY once Dorinda Medley joined the cast in season seven. Year after year, Dorinda would graciously accommodate the bunch at her lavish mansion, known endearingly as Blue Stone Manor– but it wasn’t until the season eight trip The Berkshires had transformed into “The Bezerkshires.”
The weekend’s madness started before the ladies could unpack their bags with an all-out duel between Bethenny and Luann. Queen B confronted the Countess about her shady relations with Tom D’Agostino, who shared a romantic past with Sonja and Ramona! Luann’s denial and dismissive attitude incensed Bethenny, who began their screaming match in the Blue Stone dining room.
“I’m calling you out on your s*** because no one besides me has the balls to do it,” Bethenny yells at the Countess, who responds with a fake grin, getting under the skin of the Skinnygirl mogul. “You are a slut and a liar and a hypocrite and a snake!” she continues to drive her point home and later admits she blacked out from rage and lost complete control of her acid tongue.
Luann runs to Dorinda, demanding she unleashes her duties as hostess by scolding Bethenny and giving her an ultimatum, saying she will leave if Dorinda doesn’t come to her defense. After already receiving an earful of Carole’s dissatisfaction, Dorinda completely loses her cool when Luann pokes fun at the birthday cake Dorinda’s mother provided. “If no one can behave themselves, then you’ll all go home! I give you permission, all go home! Because I decorated!” Ramona anxiously tries diffusing Dorinda, who’s past the point of consolement.
“I cooked, I made it nice! Nice! So go home everybody, go home!” Dorinda cries in utter exhaustion as Luann tries calming her down while Ramona scurries through the Blue Stone halls and demands the other women simmer down as a last-ditch effort to revive the weekend celebrations. Luann and Ramona successfully soothe Dorinda back into her happy place. Still, her meltdown would leave an everlasting imprint as RHONY fans became adoringly obsessed with Dorinda’s new slogan: “I made it nice!”
8. Turks & Caicos, Season 7
Season seven was the only time RHONY featured eight housewives, with the introduction of fan-favorite housewife Dorinda and resurrection of Bethenny, who took a three-season hiatus. With such a large bunch, heads would surely clash, and sub-groups would divide and conquer, clearly demonstrated during their cast trip to Turks & Caicos. So many little tiffs were sparked, but the fire would get stomped out quicker than it started, and the ‘Wives found themselves prioritizing their fun over the drama– a welcomed change of pace! But that all went down the drain on the fateful morning where Heather Thomson had a sunrise surprise!
After a night of booze-fueled arguments and emotional turmoil, Heather wakes up to a naked man asleep in a shared bedroom and quickly has a full-fledged meltdown. A screaming Heather wakes up Ramona and Luann, demanding an explanation. “It scared me, Luann! There was a stranger in the bed! Wouldn’t you be upset if there was a strange person sleeping in the room next to you?” Heather cries out in agony while stone-cold Luann replies: “Not really.”
“So what if I had a man in my room, I’m a grown woman I can decide for myself!” Luann mulls over in a confessional and gives Heather a piece of her mind: “It’s not a big deal! So be cool, don’t be all uncool!” Which winds up in the Real Housewives museum as one of Luann’s best one-liners and becomes a fan-favorite catchphrase throughout all of RHONY‘s glory, still beloved to this day.
7. The Berkshires, Season 9
During yet another confrontation surrounding the Housewives, Luann, and her groom-to-be Tom D’Agostino, Bethenny found herself feeling a sense of deja-vu, deep in the dramatic trenches of begging Lu to open her eyes to Tom’s cheating ways. In denial yet calm and collected, Luann wouldn’t budge, despite previous photographic evidence, and walked down the aisle just days later.
After telling Luann what they knew, the ladies threw in their proverbial towel, exhausted and ready to just have fun for once. Bethenny even offers Luann an apology for last year’s blowout, saying she has “the thickest skin of anyone she knows.” During Dorinda’s lighthearted birthday dinner, Ramona’s antics reach new levels of bizarre, acting suddenly apologetic and coo-coo for Cocoa Santas.
A blacked-out Ramona pulls practically-sober Bethenny aside to seemingly offer another apology, but Bethenny’s stoic attitude throws Ramona off course and down a deep dark hole of resentment and jealousy. “You were topless, you had sex on a waterbed, you kissed another woman, and you know what? I never mentioned it, but you know what, now we’ll mention it!” Ramona rattles off as Bethenny remains unphased.
“You wanna mention it?! Mention it all! MENTION IT ALL!” Bethenny jokes as she goes fully spread-eagle, pictured above. This moment and the phrase “mention it all” provide Bethenny with one of her most legendary comebacks, forever inked into the Real Housewives Hall of Fame.
6. Morocco, Season 4
Season four of RHONY has been widely criticized by fans and is even considered the worst season of the series by some online communities (like r/BravoRealHousewives). But there is one shining gem amongst the petulant back and forth between the “blondes vs. the brunettes,” and that is undoubtedly the cast’s vacation to Morocco.
No matter how hard they tried, this group just couldn’t band together and get on the same page. There were so many battles, from Ramona vs. Jill and Alex vs. Luann, even Kelly Bensimon vs. Sonja’s townhouse, there was hardly one moment of peace and harmony this trip. But the most epic battle had to be Luann vs. The Camel, who tried bucking her off mid-ride!
Who could forget Cindy’s stolen clothes hangers or Ramona thwarting herself onto her bed in an unconvincing-yet-pitiful fit of weeping sorrow after going toe-to-toe with Jill? Even more memorable was Alex’s ill-timed attempt at confrontation, which Luann infamously dubbed the “Herman Munster shoes” incident.
One of Morocco’s most unforgettable moments was unearthed when the ladies took turns being read by a psychic, who delivers a disturbing message to Ramona, giving a glimpse of foreshadowing into her marriage. As the French-speaking psychic delivers her reading, Ramona joyfully deciphers a few words as “another daughter,” which Luann and Kelly correct in hesitation: “no Ramona, another woman.”
Ramona’s face drops though she holds her composure as Sonja bursts into tears, which Ramona quickly writes off as Sonja still being hurt from her own marriage dissolving. Sonja unnervingly predicts: “what if your husband leaves you after your daughter goes off to college?” Ramona discovered just two years later that Mario was indeed having an affair!
5. Miami, Season 11
A quick weekend getaway to Miami, they say? Think again, say the ladies of RHONY! Fresh out of rehab, Luann’s typical condescension bleeds into her thinly veiled attempts at humility when she accuses Sonja of being on something more than just alcohol, which amplifies the group’s growing resentment towards the Countess, who storms off to her room during a heated dinner discussion on night one.
As Bethenny appears out of nowhere, she tries to “Zero Dark Thirty” the situation by deciphering what the hell she just walked into as Ramona tries to rally the troops (Sonja) for Operation Wingwoman, while Sonja continues to fall asleep at the table, making it clear she’s in no condition to co-pilot Ramona’s man-driven mission. Having flashbacks to Scary Island (see below), Bethenny urges that Sonja “go to f***ing sleep, now!” which Sonja defiantly shoots down.
During an inexplicable moment of timing that could only be explained by fate, Sonja says she’s “going to knock you out” as she takes a cumbersome fall to the ground. Traumatized by recently losing her partner to an overdose, Bethenny calls 911 in fear that Sonja hit her head during the fall. After a wellness check and confirmation that Sonja’s fall was induced purely by alcohol, Bethenny’s rage towards Luann’s cavalier accusations exacerbates her preexisting resentment, which erupts the next evening as the group reconvenes for dinner.
Bethenny usually spearheads the group as the most articulate and most put-together, but she sincerely unravels and has a true panic attack during her vicious verbal beatdown of Luann’s entitlement. “LIFE IS NOT A CABARET!” Bethenny screams at the Countess during her understandable fit of rage. “YOU’RE A SICKO!” she cries, breaking down as she realizes that maybe if she hadn’t been so engrossed in Luann’s battle with sobriety, she would’ve paid more attention to her late boyfriend Dennis’ struggles before it was too late.
4. St. Barths, Season 5
Carole planned the season five vacation to St. Barths in hopes of providing a stress-free environment for the ‘Wives to unwind. The ladies act accordingly, letting loose at a Burlesque-themed nightclub where they met a Johnny Depp lookalike named Tomas, who came fully equipped with a pirate costume and French accent (pictured below). The next morning, Heather and the other women notice Luann recounting a different tale than what actually unfolded during the night’s wee hours.
Luann tries to claim (see: lie) that she arrived home with a group of Italians, while the other women clearly recall she entered the abode speaking French, with just one man in tow! Clearly unaware of a hot mic, Luann frantically calls her friend and admits she brought The Pirate home with her– to this day, she vehemently denies any funny business happened.
Back in New York, Real Housewives Biggest Hypochondriac Aviva Drescher informs the ladies that she had a change of heart and would be joining them in St. Barths alongside her doting husband Reed, despite being deathly afraid of airplanes. While most of the women were excited about her arrival, Sonja and Ramona were dreading their girl’s trip being cut short by Reed, which infuriated Aviva as they gave the couple a lukewarm welcoming.
After Ramon-ja admits they expected Reed to stay in a hotel apart from his wife, Aviva completely loses her cool, causing Ramona to scream, “Take a Xanax! Calm down! CALM DOWN!” While Aviva continues to chew their heads off, she ends her tirade with the classic line: “you’re both white trash, quite frankly.”
3. Mexico, Season 9
While some of these excursions make the list for being outlandishly dramatic or scary, RHONY’s season nine Mexico trip stands out in a good way for being ridiculously silly, heartwarming, and just a little bit clumsy. The notorious scene of Luann falling in the bushes (pictured below) comes from this tequila-fueled fiesta after Bethenny treats the ladies to a helicopter ride and tour of her company’s agave farm. She even invites Ramona, who’s been in the dog house since their Berkshires blowout (see #7). The group finally feels whole again, just in time for them to over-imbibe in tequila samplers and Mariachi melodies.
Back at the villa, a revved-up Sonja tries to make out with Luann as Bethenny jumps in the pool butt naked, causing Sonja to follow suit (or lack thereof!). Ramona and Bethenny have a heart-to-heart in the pool, and Bethenny finally indulges Sonja’s drunken lesbian desires, giving her a soft makeout session. Unfortunately, Dorinda kills the vibe as she accidentally grabs the wrong side of a knife, causing a drunken bloodshed injury.
2. Cartegena, Season 10
Although production covers the majority of their vacationing costs, each housewife takes a turn hosting and leading the pack in their favorite destination spot. As much as Tinsley tried to raise the group’s spirits amidst the vacation she was spearheading in Cartegena, Colombia, you can’t help but notice how on-brand it is for Tinsley’s go at it to become RHONY’s most catastrophic trip yet.
Out on the town for their first group dinner, Bethenny and Carole get into a cringe-worthy spat as an exasperated Bethenny murmurs under her breath: “This is the worst vacation I’ve ever been on in my entire life.” If only Bethenny knew how much worse things would turn out! Some fans wonder if Bethenny is the curse of the RHONY vacation, but three of the ten items on this list occurred regardless of the Skinnygirl‘s inclusion!
The next morning, Tinsley anxiously gathers the group to embark on the day trip she planned, a boat ride to an exclusive offshore island. Stunned in amazement and relief, the women finally relaxed and started to finally enjoy themselves amidst the crystal-clear ocean and fully-staffed private bungalows.
They get so caught up in the island’s wonder that the boat captain nearly has to force them back on board, and what comes next was downright terrifying. The choppy waters caused so much turbulence that the cameramen and production team had to halt filming in order to remain safe– a Real Housewives first! Sirens were wailing, Carole was uncontrollably puking, and the ‘Wives barely made it to shore after the anchor got stuck, which the captain luckily cut free with a pirate’s sword! After some PTSD and partying the night prior, most of the women woke up with explosive diarrhea, as if things couldn’t get any worse for this group!
1. Scary Island, Season 3
It will come as no shock to any Real Housewives fan that Kelly Bensimon’s major meltdown à la Scary Island reigns as the number one most iconic vacation in RHONY history. The weekend getaway to St. John was originally intended as a celebration for Ramona’s upcoming vow renewal to commence her 17th (yes, 17th) wedding anniversary. It was drastically apparent that Kelly started off the trip being defensive, hostile and clearly had it out for Bethenny, insulting the pregnant Skinnygirl owner left and right. From saying it was “creepy,” B was vacationing soon after her estranged father passed away, to labeling her a “cook, not a chef” and calling her names like “slut” and “whore”, Kelly berated Bethenny nonstop.
However, things took a turn for the much worse during an episode appropriately titled “Sun, Sand, and Psychosis.” In between babbling nonsense about satchels of gold, 1979, and Al Sharpton, Kelly unleashed some serious accusations about Bethenny, saying she was trying to ruin her children’s lives and claiming she had tried to kill her many times before.
But as she’s making these bold claims, she just as quickly drops the act and begins giggling and skipping to her room to grab jelly beans. Bethenny infamously screams, “Go to sleep! GO TO SLEEP!” at Kelly, fed up with her instability, but Sonja realizes they have a much bigger problem on their hands, urging the other Housewives to stop taunting her because she was legitimately having a mental breakdown.
After Sonja addresses her concerns, the cameras go down, and there’s a quick mention of Kelly being escorted home by producers. She wasn’t checked into any sort of facility, and she returned filming as if nothing that out of the ordinary happened during their St. John trip, later renamed “Scary Island” by fans and fellow castmates. Some fans believe Kelly was experiencing a meth-induced psychosis, while others think she just had a mental breakdown, but only the cast and crew know the haunting and surreptitiously salacious details that never left the cutting room floor.
