Kaitlyn Dever and Dominic Sessa: “The phone charger arrived on a silver tray”

There’s something of the fairy tale to 21-year-old Dominic Sessa’s rise to fame. When acclaimed Sideways director Alexander Payne was casting for his 2023 film The Holdovers, a bittersweet tale set in a wintry New England boarding school, he chose Deerfield Academy in Massachusetts to serve as the main location. As a young drama student at the school, Sessa decided to chance his luck and audition. Out of nowhere, he won a leading role, and gave a career-making performance.

By contrast, fellow actor Kaitlyn Dever, 27, has established herself as a force over the course of a decade, in acclaimed film and TV projects including Booksmart, Dopesick, and Unbelievable. Dever is currently in production on the second season of the post-apocalyptic masterpiece The Last of Us. 

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Thanks to their profession, both actors have spent more than their fair share of time in hotels, especially when filming on location. But it’s clear that Sessa and Dever recognize that there’s more to a hotel than a mere bed to sleep in, and that the best places can provide special memories that last.   

“Once a year, my mom would take my sister and me away on a special girls’ trip to Texas,” Dever recalls, “and the whole idea was that we’d stay in a Hampton Inn, go shopping, and then go back to our hotel and do scrapbooking together.

“And it’s good that I was able to repay that; for Mother’s Day one year, I took her away to the Calamigos Guest Ranch. It’s a really quiet and peaceful place in the canyon of Malibu, with its own lounging area on the beach where you can get drinks and tacos. It feels really luxurious.” 

Sessa, a New Jersey native, also has a favorite place to stay in California. “I grew up not far from Atlantic City, so I’m a beach person and a surfer. There’s a place called Shutters on the Beach in Santa Monica, and I like the shore-condominium architectural look of the place. It has such a nice vibe that reminds me of houses by the coast when I was growing up.”

Naturally, they both also appreciate a touch of five-star luxury. “I was in Paris for a show,” says Sessa, “and I got to stay at the Crillon. It was one of the most regal hotel experiences I’ve ever had, with an amazing room and great views of the Eiffel Tower. I remember asking them to send up a phone charger and they brought it up on a silver tray, which was pretty unprecedented.”  

Dever appreciates it when the hotel’s setting adds to its charm: “There’s a great spa resort in the Hamptons called Gurney’s where you feel like you’re literally on the edge of the United States, in your own world. The rooms have really beautiful views; the beach is so vast and desolate, so it’s the perfect place to unwind and just go walking on the sand with your dog.” 

When preparing for travel, Dever and Sessa have two very different routines. Dever is regimented: “I try to be dialed-in with my packing. I have miniature sizes for my hair products and I fold my clothes into packing cubes. Then, the moment I get into my room, I hang everything in the closet, or else I can never find an outfit.”

Sessa describes himself as a “chronic under-packer.” “I hate waiting for my luggage at the airport, so I won’t even take spare socks and underwear—I just buy it at my destination. And unless I’m staying for more than four weeks, my stuff is staying in my suitcase. On the downside, I can never find things, and I end up wearing the same outfit for three days in a row!”

As for their bucket-list stays, Sessa’s is close to home, but cinematic. “I’ve never stayed at The Plaza, which is so iconic. Home Alone was one of my favorite movies growing up, and running around the corridors like Macaulay Culkin has been a fantasy of mine. I still want to do it!” he says. “Otherwise, I’d love to stay at the Lodges at Crest Haven, up in the Adirondacks. It’s known for water activities on the lake, but they also have a golf course. The views are so beautiful that even if you were playing terrible—as I do—they would make up for it.”  

Michael Smith

Writer

Michael Smith has been a journalist for titles including the Financial Times, GQ, Esquire and FHM, as well as presenting numerous travel series on British television, which saw him exploring the Amazon in Brazil, swimming with sharks in South Africa, and skydiving in Australia.