14 Photos of the Kardashian-Jenners on Luxurious Vacations
14 Photos of the Kardashian-Jenners on Luxurious Vacations
Amelia Langas, Emily KrauserTue, April 21, 2026 at 11:00 AM UTC
0
L to R: Kendall Jenner, Khloe Kardashian, Penelope Disick, Mason Disick, Khloé Kardashian, Kourtney Kardashian, Kris Jenner and Corey Gamble in Wyoming in 2020Credit: Kim Kardashian/Instagram
Just add professional jetsetter to the multi-hyphenate Kardashian-Jenners.
Kim Kardashian, Kourtney Kardashian, Khloé Kardashian, Kendall Jenner and Kylie Jenner, along with mom Kris Jenner, have all taken memorable trips together, as well as some lovely excursions with their own kids.
The vacation heard around the world will always be the 2011 Bora Bora getaway, seen during a season 6 episode of Keeping Up With the Kardashians, when Kim famously lost a $75,000 diamond earring.
There were plenty more with seemingly less drama, including Kylie's daughter Stormi's epic 3rd birthday celebration in Turks and Caicos a decade later, many trips to Italy by multiple family members and more recent outings by Kylie to Greece and Kim to Spain.
They've stayed stateside too, skiing in Utah and experiencing ranch life in Wyoming.
Keep reading to revisit their most memorable, luxurious — and occasionally chaotic — vacations through the years.
01 of 14
Bora Bora
Kim Kardashian loses an earring in Bora Bora in a scene from 'Keeping Up With the Kardashians'Credit: E!
Let's revisit a classic KUWTK moment from when the family was in Bora Bora, and Kim famously lost one of her $75,000 diamond earrings in the Tahitian ocean.
And thus was born a line embedded in the cultural zeitgeist: "There's people that are dying, Kim." Thank you, Kourtney!
02 of 14
Vail, Colorado
The Kardashian-Jenner family skiing in Vail, Colo., in 2016Credit: Kris Jenner/instagram
The famous family has a long history of vacationing in the Colorado ski town. Kris posted this photo of the squad outfitted in skiing gear in Vail in 2016.
03 of 14
Cannes, France
Kourtney Kardashian and Kendall Jenner on a boat in France in 2017Credit: Kourtney Kardashian/instagram
The Cannes Film Festival draws stars to France every year, and the Kardashians aren't left out. While there in 2017, Kourtney and Kendall relaxed on a boat away from the crowds.
04 of 14
Japan
Kourtney Kardashian and Khloé Kardashian in Japan in 2018Credit: Kourtney Kardashian/instagram
In March 2018, Kim, Kourtney and Khloé tried something new and visited Japan — just one month before Khloé gave birth to her first child, daughter True.
Among the places the sisters visited were Tokyo and Kyoto.
Kim returned to Tokyo with her oldest child, daughter North, in 2023. She took another trip back with her three younger kids — sons Saint and Psalm and daughter Chicago — for their spring break, a source told PEOPLE.
Also there for the latter visit were Kim's rumored boyfriend Lewis Hamilton —the outing took place shortly before the F1 driver competed in the Japan Grand Prix in late March 2026 — and Khloé and her children, daughter True and son Tatum.
05 of 14
Costa Rica
Kourtney Kardashian with daughter Penelope Disick and son Reign Disick in Costa Rica in 2019Credit: Kourtney Kardashian/instagram
After a dip in the ocean while in Costa Rica in 2019, Kourtney snuggled with her two younger kids with ex Scott Disick, daughter Penelope Scotland and son Reign Aston.
(Kourtney also shares older son Mason Dash with Disick and has a younger son, Rocky Thirteen, born in 2023, with husband Travis Barker.)
06 of 14
Wyoming
L to R: Kendall Jenner, Khloe Kardashian, Penelope Disick, Mason Disick, Khloé Kardashian, Kourtney Kardashian, Kris Jenner and Corey Gamble in Wyoming in 2020Credit: Kim Kardashian/instagram
Yeehaw! Kim's ex-husband, Kanye West, with whom she shares all four of her kids, bought the Wyoming ranch where the Kardashians spent much of 2020.
West owned two ranches in Wyoming. He purchased Monster Lake Ranch, near Cody, Wyo., in September 2019, and it has been on the market since 2021.
He sold back his second, Bighorn Mountain Ranch, also purchased in 2019, to its original owners in the fall of 2025.
Though the rapper spent more time in Wyoming than the rest of his family, Kim and their children visited the Cowboy State many times.
07 of 14
Canyon Point, Utah
Kylie Jenner at the Amangiri Resort in Canyon Point, Utah, in 2020Credit: Kim Kardashian/instagram
Canyon Point is home to a celeb-loved hideaway known as the Amangiri Resort. Kylie escaped to the desert in July 2020, captioning an Instagram slideshow from her stay, "I love it here."
Advertisement
Her sisters have also stayed at the luxury five-star hotel in Utah.
08 of 14
Aspen, Colorado
The Jenner sisters ride snowmobiles in Colorado in January 2021Credit: Kylie Jenner/instagram
Aspen is a well-known getaway spot for the rich and famous.
Kylie, Kendall, and Kris kicked off 2021 at the Rocky Mountains hotspot, where the younger Jenners tried their hand at snowmobiling."What a way to start the year," Kylie captioned Instagram photos from the excursion.
09 of 14
Deer Valley, Utah
Reign Disick and Kourtney Kardashian in Deer Valley, Utah, in April 2021Credit: Kourtney Kardashian/instagram
For spring skiing, Kourtney took a 2021 trip to one of the Kardashian clan's favorite haunts: Deer Valley.
She captioned an Instagram slideshow with son Reign simply, "chilling."
10 of 14
Turks and Caicos
North West, Kim Kardashian and Chicago West in Turks and Caicos in 2021Credit: Kim Kardashian/instagram
For Kylie's daughter Stormi's 3rd birthday in 2021, all the girls, minus Kendall, took a trip to Turks and Caicos.
Kim shared a trio of Instagram photos from the trip with daughters North and Chicago, which she captioned "Girls Trip!"
The tropical island was a frequent repeat for Kylie, especially for birthdays.
11 of 14
Italy
Khloe Kardashian and Kris Jenner in Italy in August 2023Credit: Khloe Kardashian/Instagram
Various members of the family head to Italy nearly every summer.
During a trip in August 2023, Khloé pouted for the camera as Kris flashed a smile as they took a selfie in front of a gorgeous vista at what appears to be sunset. The Good American co-founder captioned her Instagram post, "🤍Me and my favorite girl 🤍."
Beyond that trip, the KarJenner clan has shared many photos from their Italian excursions, as Kourtney did during her trip to Portofino in 2019 — which is also where her wedding to Barker took place in May 2022 — and Sardinia in 2020.
Kylie has also shared numerous images from trips to Italy. Among those include her 22nd birthday on a yacht and a visit with her kids in July 2025.
She captioned an Instagram slideshow of the latter, "italian summer yes pleaseeee 🤍🤍🤍🤍🤍🤍."
12 of 14
Spain
David Alaba, Jude Bellingham and Kim Kardashian at the Real Madrid headquarters in Spain in August 2024; Kim Kardashian's son Saint in a signed soccer jerseyCredit: Kim Kardashian/Instagram
In August 2024, Kim jetted off to Spain with son Saint, a huge soccer fan, and some of his friends to visit the Real Madrid headquarters.
The SKIMS founder snapped a selfie with two soccer pros, David Alaba and Jude Bellingham, and Saint even got his jersey signed by some of the players.
Kim also posted more group shots that included her posing with her son and friends in a crew that included Real Madrid's Eduardo Celmi Camavinga and Vinícius Júnior and the musician Savas.
13 of 14
Greece
Left: Kylie Jenner in Greece in July 2025; Right: Stormi Webster and Kylie Jenner in Greece in July 2025Credit: Kylie Jenner/Instagram
The summer of 2025 involved a lot of jetsetting for Kylie, who shared many photos from the gorgeous locations she vacationed in. One of those was Greece, where she adventured with her kids and some friends.
Among the photos she shared in an Instagram slideshow were poses in a yellow bandana bikini and a shot of her splashing around in the water with daughter Stormi.
14 of 14
Cabo San Lucas, Mexico
Kim Kardashian shares photobooth pictures from a trip to Cabo San Lucas, Mexico, on Instagram in August 2025Credit: Kim Kardashian/Instagram
Kim jetted off to Cabo with her children and some friends in August 2025.
She shared more than a dozen photos from the trip, including a picture with Saint, Chicago and Psalm smiling for the camera as they cuddled up in blankets on a private jet and a collection of photobooth photos taken by her kids.
While Khloé didn't make the trek, her children, True and Tatum, joined their aunt and cousins for the vacation.
on People
Source: “AOL Entertainment”
