In most seasons of The Real Housewives, the women typically go on a vacation getaway of some sort for a few days. Being outside of their comfort zone really has an effect on the women, as they have to get used to a time change, culture differences, language barriers, and, at times, rooming with someone else. For the women of New York, when an island getaway isn’t possible, they tend to take their holiday to the Hamptons or the Berkshires.
There have been countless iconic moments at Dorinda Meadley’s home in the Berkshires, and the same could be said for Ramona Singer’s Hamptons home. However, the best vacations are when the women hop on a plane and get off of the East Coast.
10 Turks & Caicos (Season 7)
Compared to other trips, Turks & Caicos was a rather relaxed time in season 7. With Ramona newly single, she was taking her life outside of Mario one step at a time.
Sonja, on the other hand, was enjoying the single life, which caused her friends to worry and judge her decision-making. Sonja’s personal life soon became the topic of every scene. Thanks to the repetitive nature of the conversations, this vacation was stunning—but not the most entertaining.
9 London, England (Season 5)
In season 5, only a few of the women traveled to London: Luann, Carole, Heather, and Sonja. As it turns out, the smaller group made for a much better trip. Carole and Luann did get into a few arguments when Carole felt that Luann was one-upping everyone else, which became irritating.
Carole was right in the fact that Luann loved to compare her experiences with others. However, the group got over their bickering and had a fantastic time. While there wasn’t the typical drama or drinks, this was a relaxed, well-planned vacation.
8 Montana (Season 6)
Going to Montana as a group was a first for the women. They made it known that they were from New York and not country folk. Every Housewife save for Heather and Carole judged the area for its lack of luxury and expected more in every area. Ramona kept repeating how “bored” she was. Furthermore, Aviva’s absence caused quite a stir because she claimed she couldn’t fly because of asthma.
The first night was plagued with gossip regarding Sonja’s facialist, which caused a fight between Luann and Sonja, but things got better. They went fly-fishing, rock climbed, shooting, and enjoyed a rodeo. As fun as it was to see these women in the Midwest, most loathed every part of this trip.
7 The Berkshires, Massachusetts (Season 8)
The trip to the Berkshires wasn’t necessarily a great one for the women, but season 8’s ‘December: Berkshires County’ was one of the most iconic episodes in RHONY history. Bethenny and Luann were fighting like cats and dogs, and Luann mentioned that she helped Bethenny with her mega-brand, Skinny Girl. From there, Luanna and Ramona started bickering about who dated Tom first.
The breaking point was when Luann made fun of Dorinda’s homemade birthday cake, created by Dorinda’s mom. After decorating, cleaning, and cooking, Dorinda felt disrespected and told everyone to go home. It wasn’t the Berkshires’ best moment, but it’s one of those episodes fans watch again and again.
6 Cartegena, Colombia (Season 10)
Tinsley brought her A-game when she invited the women to Cartegena, Colombia. As gorgeous as the home was, the first day was met with drama immediately. Bethenny had an allergic reaction to fish stew, Ramona got stuck inside an elevator, and Bethenny and Carole got into a big fight over dating the same guy.
The second day had a better start but ended with a disastrous dinner. Luann poked fun at Dorinda’s drinking at one side of the table while Bethenny and Carole were bickering at the other end. As gorgeous as the environment was, no one was getting along, and it got worse. The following day, the women were in a panic when they realized they were on a capsizing boat. Everyone was in tears, hanging on for dear life until they made it to shore. As always, some of the worst trips make the best episodes.
5 Miami, Florida (Season 11)
The women of New York have vacationed in Miami on two occasions, once in season eight and once in season 11. On both occasions, they revolved around Luann. In season 8, Luann found out that her fiance cheated on her and two seasons later, Luann was divorced from the same man and on a downward spiral.
Between the two, season 11’s trip reigns supreme over season 8. There were so many different, dramatic storylines at play during this RHONY saga. Sonja injured herself at dinner, resulting in an ambulance coming to the house, Ramona came face to face with Mario at a house party, and Bethenny gave Luann the speech of the century when she told her “life wasn’t a cabaret” and that she needed to deal with her problems head-on.
4 Morocco (Season 4)
In the fourth season, Morocco was the destination of choice for the women of New York. Being so far away from home in a culture that was different from their own, fans knew some outlandish things were bound to happen. One night, the women went to a fortune teller where Ramona was told that there was another woman in his life. As fans know, that turned out to be true in later years and was the reason for their divorce.
Later, Luann was almost bucked off a camel, creating one of the most memorable RHONY moments, Jill and Ramona got into a crying match over their friendship, and Luann’s planned dinner was ruined when only a few of the women showed up. A wonderful trip to an exotic land was derailed thanks to varying arguments, but it made it entertaining for viewers.
3 St. John, Virgin Islands (Season 3)
The St. John trip is best known as “Scary Island.” For Bethenny, it was a hard time for a vacation because her dad had just passed away and her friendship with Jill was over. Meanwhile, things began to transpire with Kelly Bensimon. She slowly acted out of character and was saying these quotes that didn’t necessarily make sense or add up.
Things got out of control when Kelly accused Bethenny of trying to kill her, which left Bethenny gobsmacked. To tie the whole trip up in a dramatic bow, Jill surprised the group unannounced. Considering the number of tears and arguments they had, Jill’s presence was too much too soon, and the women sent her home.
2 St. Barts (Season 5)
In season 5, the women flew to St. Barths to spend some time in the sun. As always, things started out happy, and everyone was on the same page, but that changed as the vacation went on.
One night, the group goes out for a pirate-themed clubbing adventure. The following day, Heather told the cameras that Luann came into her room at 3 am with a man. Considering the fact that Luann had a serious boyfriend at the time, fans saw this as one of her more shocking decisions on Real Housewives. The drama continued when Aviva Drescher showed up to the vacation late with a special guest—her husband. Adding a husband into the mix of a girls’ weekend changed the dynamic drastically.
1 Mexico (Season 9)
When Bethenny had to travel to Mexico for a business trip, she turned it into a girls’ getaway to taste-test tequila and let loose. The first day was typical, with Sonja and Ramona running around trying to pick the best room. Luann even fell into a few bushes after having too much to drink.
However, the real fun started when they went to the tequila plant. Fans knew Bethenny was the creator of a massive alcohol brand, but they didn’t know how involved she was until this trip. For once, it was fun to see the women have a fun time and all get along.