Jared chose black bottoms with a long sleeved white shirt, adding a straw hat and sneakers.
He followed Kelsey closely behind as they climbed a rock wall together during their vacation activity, stopping at Tavolara Island off the northeast coast of Sardinia for their adventure.
The duo were joined by someone who appeared to be a tour guide or rock climbing instructor as he also directed their boat to the rock climbing location.
Jared and Kelsey have been staying on a mega yacht with fellow Victoria's Secret models Jasmine Tookes and Izabel Goulart.
Kelsey showcased her incredible model figure in a black belted bathing suit with a halter neckline.
She added rock climbing anti-slip type socks with an anklet, opting to wear her hair back into a bun.
Kelsey, who is currently based out of New York City, has been featured in Sports Illustrated's Swimsuit Issue as well as named the first Filipino-American to walk the Victoria's Secret Fashion Show runway, which she did in 2018.
The brunette, who has over 1.7 million Instagram followers, revealed on Monday she tried scuba diving for the first time.
She also posted snaps from their lunch in Cala Di Volpe.
It is unknown if the duo are dating; Jared has previously been linked to Cameron Diaz, Katy Perry, Lindsay Lohan, Scarlett Johansson and Ashely Olsen, as well as model Valery Kaufman.
She dated Olympian Conor Dwyer from 2018 until they seemingly split earlier this year.
Supermodel Izabel Goulart was also a guest on the giant yacht.
The Brazilian bombshell wowed in a bright red string bikini, opting to tie the triangle top behind her to avoid tan lines across her chest.
The runway star, 37, added a black visor and gold hoops for a stunning yacht look, wearing her brunette hair back into a ponytail.
Fellow Victoria's Secret model Jasmine Tookes was seen chatting with her husband Juan David Borrero.
Jasmine, 31, looked gorgeous in an olive hued top with white jeans, opting for a white necklace and pulled back tresses.
Jasmine and Juana married in Quito, Ecuador in September 2021.
They met in 2016; Juan works as a Snapchat executive and met Jasmine and several other models that year for lunch over a new feature for the app they wanted them to promote, according to Vogue.
