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Us Looks Back at Taylor Swift’s Vacations With Boyfriends Over the Years

by Staff

Island breeze and lights down low! Taylor Swift has been known to take romantic getaways with her significant others over the years.

Swift and Joe Alwyn were notoriously private during their six-year relationship — Us Weekly confirmed their split in April 2023 — but when they were spotted getting cozy, it was often on vacation.

In June 2022, Swift and Alwyn were photographed kissing with their arms wrapped around each other while going for a swim in The Bahamas.

Alwyn was not the first — or the last — to enjoy an amorous trip with the pop star. Join Us for a look back at Swift’s lovestruck trips over the years:

Utah With Harry Styles

Let’s travel back in time to December 2012. Selena Gomez and Justin Bieber are still together, and they’re taking a ski trip to Park City, Utah, with Styles and Swift. A source told Us at the time that the two duos stayed in separate houses at The Colony but hit the slopes together at Canyons Resort.

Styles shared photos via X at the time that showed him smiling with a bandage on his chin, which some Swifties believe to be the result of a snowmobile accident he got into with Swift.

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Swift opened up about getting into a snowmobile crash with an ex — although she didn’t identify Styles by name — during an October 2014 interview with Rolling Stone. She said she was “not as hurt” during the crash as her beau and offered an explanation for why the accident didn’t make headlines at the time.

“You know what I’ve found works even better than an NDA? Looking someone in the eye and saying, ‘Please don’t tell anyone about this,’” she said.

Swift alluded to the incident in the 1989 track “Out of the Woods,” singing, “Remember when you hit the brakes too soon? 20 stitches in a hospital room.”

Virgin Gorda With Harry Styles

Taylor Swift’s Vacations With Boyfriends Through the Years

David Krieger/Bauer-Griffin/GC Images

Shortly after their trip to Utah, Swift and Styles jetted off to Virgin Gorda, the third-largest of the British Virgin Islands, in January 2013. A source told Us at the time that trouble broke out in paradise, leading to the twosome’s split.

“They had a fight,” the insider said, noting that Styles “said something he shouldn’t have” and the romance was “100 percent over.”

A photo from the ill-fated vacation, which showed Swift sitting sadly by herself on a boat, made the rounds online at the time. Swift seemingly nodded to the viral picture — and the snowmobile accident — on the 1989 vault track “Is It Over Now?” which was released in 2023 on 1989 (Taylor’s Version).

“When you lost control, red blood, white snow / Blue dress on a boat, your new girl is my clone,” she sang.

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London With Calvin Harris

Taylor Swift’s Vacations With Boyfriends Through the YearsTaylor Swift’s Vacations With Boyfriends Through the Years

James Devaney/GC Images

Swift proved that she no longer had an axe to grind against ex-boyfriend Joe Jonas, whom she dated briefly in 2008, when she enjoyed a boat ride down the River Thames with him in 2015.

Swift shared a photo of the outing via Instagram at the time. She sat with her arms around then-boyfriend Harris while Jonas sat next to then-girlfriend Gigi Hadid. Swift’s then-best friend Karlie Kloss looked happy to be a fifth wheel, smiling with her arms resting on the boat.

 

Tropical Getaway With Calvin Harris

“That time when we finally took a vacation. @calvinharris,” Swift wrote via Instagram in March 2016 alongside several since-deleted snaps of herself and Harris in an undisclosed tropical location.

In the photos, Swift and the Scottish DJ, who dated from 2015 to 2016, kissed by the ocean, jumped on a giant water trampoline and posed by jet skis.

 

Rome With Tom Hiddleston

Taylor Swift’s Vacations With Boyfriends Through the YearsTaylor Swift’s Vacations With Boyfriends Through the Years

INF/INSTAR

After she split from Harris in June 2016, Swift had a brief whirlwind romance with Hiddleston. Just weeks into her single era, Swift toured the Vatican in Rome with the Loki star. The twosome were seen holding hands and taking pictures of each other as they went sightseeing through the city.

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Turks and Caicos With Joe Alwyn

Taylor Swift’s Vacations With Boyfriends Through the YearsTaylor Swift’s Vacations With Boyfriends Through the Years

Jackson Lee/GC Images

Swift and Alwyn looked happy and in love while walking down a Turks and Caicos beach in July 2018. The singer wore a blue and white striped bikini, holding a drink in one hand and Alwyn’s hand in the other.

The Bahamas With Joe Alwyn

There’s no doubt that Alwyn was once the king of Swift’s heart, as evidenced by photos of the pair locking lips in the ocean during a June 2022 trip to The Bahamas.

The Bahamas With Travis Kelce

Taylor Swift’s Vacations With Boyfriends Through the YearsTaylor Swift’s Vacations With Boyfriends Through the Years

Gotham/GC Images

Swift returned to the Caribbean locale in March 2024 — but this time, she brought along Kelce. Photos shared via gossip blog Deux Moi showed the musician and the NFL star, who started dating in 2023, on a stroll through a harbor.

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