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The Messiest ‘Real Housewives’ Girls Trips in Bravo History: Scary Island, Napa Valley and More

The Messiest Real Housewives Girls Trips in Bravo History 277
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After nearly two decades of The Real Housewives, there are several things you can expect from every season: designer handbags, theme parties and girls trips.

While every girls trip is special, each city has a few that stand out above the rest as more dramatic, more deranged and more likely to end up quoted on unofficial Etsy products. To paraphrase Tolstoy: Each messy girls trip is messy in its own way.

One of the series’ most famous girls trips — Scary Island from RHONY season 3 — was as stressful behind the scenes as it looked on TV. “We’d never taken the Housewives on the road before,” producer Matt Anderson recalled during a panel discussion at BravoCon in 2022. “I didn’t know what it would be like to take care of them 24/7, and it was hard.”

Anderson quickly realized that there weren’t enough producers to handle all the shenanigans — and when the trip was finally over, he needed a break too. “It was like nothing I’d ever seen before,” he said. “It was right before Thanksgiving break, and I slept for four days straight.”

Scary Island is in a class of its own, but there are plenty of other vacations worthy of a rewatch or five. Keep scrolling for an (unranked) look back at the messiest girls trips in Real Housewives history:

New York City: Scary Island

The RHONY cast’s season 3 trip to St. John was billed as a second bachelorette party for Ramona Singer, who was about to renew her vows with then-husband Mario Singer. While Ramona did coin the phrase “turtle time” during this trip, the fact that it was her party was soon lost in a sea of truly deranged moments, most notably the scene where Kelly Killoren Bensimon and Bethenny Frankel got into a screaming match that for some reason mentioned Al Sharpton and ended with Bethenny yelling, “Go to sleep!” And that’s all before Jill Zarin crashed the party after previously telling Ramona she couldn’t come. Pass the gummy bears, because this one is staying in the queue forever.

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New York City: Slutty Island

Nothing can top Scary Island, but Slutty Island — a.k.a. St. Bart’s — came close. In season 5, the RHONY gals returned to the Caribbean for another boozy getaway. This is the one where Luann de Lesseps brought home the pirate, though she has long denied that anything untoward happened between the pair (she was dating Jacques Azoulay at the time). It’s also the one where Aviva Drescher brought her husband, which was a flagrant violation of one of the cardinal rules of girls trips: no husbands!

New York City: Morocco

In season 4, the ladies traveled to Marrakech, where they tried regional cuisine and embraced local culture by riding camels. Also, they fought about the number of hangers in their closets and Luann said Alex McCord sounded like a buffalo coming down the stairs.

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New York City: The Berzerkshires

The RHONY cast has been to Dorinda Medley’s Berkshires home multiple times, but the season 9 trip takes the cake as the most iconic thanks to her legendary breakdown: “I decorated, I cooked, I made it nice!” Even Andy Cohen was impressed. “It is a speech that anyone can relate to,” he later said during an episode of Watch What Happens Live With Andy Cohen. “This woman broke her back to have her friends come over. She cooked. She cleaned. She made it nice. And these bitches are disrespecting her at every step of the way [and] her mother’s cake — and she broke.”

New York City: The Hamptons

In season 12, the RHONY wives joined Ramona at her home in the Hamptons. So far, so traditional — until Leah McSweeney got fully naked and started uprooting Ramona’s tiki torches. “These represent bad things,” she claimed. “You don’t read the news enough.” (She later explained that she associates tiki torches with a 2017 white supremacist rally in Charlottesville, Virginia, that left one person dead.)

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Salt Lake City: Vail

Salt Lake City is one of the younger Housewives franchises in the mix, but its cast has wasted no time in getting some iconic girls trips in the books. Case in point: the season 2 trip to Vail, which popped off before the wives even left the Beauty Lab parking lot. As the ladies were gearing up for another sprinter van journey, the FBI arrived in search of Jen Shah, who had already left to see about husband Sharrieff Shah’s “internal bleeding.” Jen, who was soon arrested, didn’t make it on the trip, but everyone else did — including Meredith Marks, who coped with the news by taking a bubble bath.

Salt Lake City: San Diego

Confined to the United States because of Jen’s pending trial, the women of SLC traveled to exotic San Diego in season 3 — and soon learned that enough rosé can make any destination worthwhile. This was especially true for Heather Gay, who ended up with a mysterious black eye that everyone else thought was caused by Jen. (Heather said it wasn’t.) As of September 2023, it is still not known who or what caused the black eye.

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Salt Lake City: Palm Springs

As of this writing, the SLC cast’s season 4 trip to Palm Springs is still airing, but it already has all the makings of an all-timer. Someone showing up uninvited? Check. Someone taking the best room from the hostess, even though this is quite literally a hotel and thus does not belong to the hostess in question? Yes, and do not question the rules of Housewives trip hostessing. But most importantly, it has the rumors, the nastiness and Heather puking into a bag in the back of a Sprinter van while wearing a hat that says “Cat Mom.”

Beverly Hills: Amsterdam

During a cast trip to the Netherlands in season 5, Lisa Rinna and Kim Richards had it out over dinner after Lisa asked one too many questions about Kim’s recovery. After Kim called Eileen Davidson a beast and the wine glasses started flying, Kyle Richards understandably fled the scene.

Beverly Hills: Aspen

RHOBH is known more for its wild dinner parties than its girls trips — see season 1’s astonishingly good “Dinner Party From Hell” — but the season 12 voyage to Aspen went a long way to changing that perception. The women had an onscreen tiff about Kathy Hilton’s tequila, but the biggest drama happened off-camera, when Kathy and sister Kyle had a blowout fight so big that they didn’t speak for months.

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Potomac: Cayman Islands

The RHOP cast’s season 4 excursion to the Cayman Islands was full of delicious drama, but the moment that really stands out is the lobby fight between Karen Huger and Gizelle Bryant over Karen’s use of Instagram Live. As other unsuspecting hotel guests looked on, the pair got so heated that Gizelle threatened to change her room reservation while Karen called her costar a “phony.” Ashley Darby, meanwhile, just wanted to know how things had unraveled so quickly.

New Jersey: Napa Valley

The RHONJ cast’s season 4 road trip through Napa Valley wasn’t technically a girls trip because the husbands were invited, but an exception must be made because of how many ridiculous things happened. After spending way too much money at Camping World, they engaged in a cookoff between the families made all the more difficult by the fact that they had to do all their prep in their tiny RV kitchens. Most shocking, however, was the moment when Teresa Giudice’s then-husband, Joe Giudice, referred to her as his “bitch wife” and a “c–t” during a mysterious phone call. Teresa should have left him at Camping World.

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Atlanta: Anguilla

In season 5, the women of Atlanta decamped to Anguilla, where they kicked things off with a boat ride so horrendous NeNe Leakes threatened to call the police. This trip ostensibly commemorated the wedding of Cynthia Bailey and Peter Thomas, but their nuptials were completely overshadowed by the sight of Kenya Moore twirling away from a fight while telling her costars she was “Fabulous! Gone With the Wind fabulous.”

Atlanta: South Carolina

Three words: Bolo the stripper.

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Orange County: Bali

Any girls trip that involves the Housewives interacting with exotic animals is an A+ in Us Weekly’s book, and RHOC’s season 9 trip to Bali delivered with the ladies taking a ride on an elephant. Also iconic? Vicki Gunvalson and Shannon Beador trying to kayak while enjoying cocktails.

Orange County: Ireland

From the minute Kelly Dodd failed to realize that Irish people speak English, it was clear that this season 11 RHOC trip would be one to remember. Another key moment came when the ladies donned hazmat suits so they could milk cows at the Bailey’s Irish Cream factory.

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