(CNN) — Jason Salesberry had never set foot on Italian soil before moving there in October 2017. Today, he owns a house in a hilltop town and is planning the harvest from his two-acre grove of olive trees.
In the nine years since his family arrived in Naples sight unseen, their life has transformed into a whirlwind of European adventure — from paragliding in Switzerland and scuba diving in Greece to days enjoying the local beach and Neapolitan gelato.
“Living in the heart of Europe has unlocked a world of adventure for our family,” Jason tells CNN Travel today.
It is a life the US Navy veteran, who grew up in San Diego, California, and was previously stationed in Puerto Rico and Japan, had never predicted. But he had long been fascinated by Italian culture and dreamed of one day experiencing it firsthand.
After meeting his wife Sherry, a fellow US Navy veteran originally from Trinidad and Tobago, and settling down to start a family, that dream became an active plan.
A leap into the unknown
“I never imagined my life’s path would lead to a hilltop town in southern Italy,” Jason says.
“It really was just an adventure. We wanted to try something new.”
There were practical motivations, too. Jason says he had grown increasingly concerned about violent crimes in Chesapeake, Virginia, where the family had been living since 2009. He wanted a safer, more stable environment for his young daughter.
“When I compared European crime rates to those in the US, the decision became clear,” he says. He applied for a position at a military base near Naples and was hired shortly after.
But while Jason was eager to leap into the unknown, Sherry required some serious convincing.
“I pretty much protested on coming here,” Sherry admits. She eventually agreed to the move on one strict condition: they would stay for only three years. “I’m an only child, and my mom did not want me to come.”
Because they viewed the relocation as a temporary assignment, they kept their three–bedroom home in Virginia rather than sell it. They packed light, unsure of what to expect from Italian housing.
In October 2017, they arrived in Naples with their daughter and their dog. They were anxious about the move in the beginning and couldn’t help but wonder if they’d made the right decision. Jason vividly recalls their first night in the country when the “sheer weight of unfamiliarity” left Sherry in tears.
They eventually found a rental home on the US Navy complex in Pozzuoli, an historic town situated directly on a volcanic caldera. It offered fabulous views, but also isolated them from local life “in an American bubble.”
Learning to slow down
As they settled in, the family fell in love with the local food scene and the slower pace of life in Naples.
“Back home in the US, everyone’s busy,” says Sherry. “You have your nine to five, then you have to prepare to go to school and work the next day. It’s not like that here.”
She jokes that they had to learn to adapt to a local culture where a dinner can last two or three hours.
“We had to learn the art of slowing down,” adds Jason. “Yet, the benefits have far outweighed the adjustments.”
As the birthplace of pizza, Naples offered plenty of culinary exploration. The family loved trying out the city’s mom and pop restaurants, marveling at how every kitchen had its own spin on classic pasta and pizza.
But local schedules brought some culture shock.
Restaurants rarely opened for dinner before 7.p.m. — a time when the family was typically winding down. Adding to the challenge, Jason and Sherry, who works for bank, often maintained US office hours.
Then there was the traffic. The “intense” driving style in Naples left Sherry so terrified it took her eight months to muster the courage to get behind the wheel.
“I still can’t get used to it,” she says, explaining that she finds local drivers to be very “unpredictable” and has her “head on a 360 swivel” constantly. “In America, you know what the other driver is doing,” she says. “Here, they do whatever they want.”
Even the local waste management system proved to be a minefield, requiring trash to be separated into five different categories, with rules changing from one neighborhood to the next.
On the financial side, the family found that their dollars stretched significantly further than they did in Virginia. The lower cost of fresh produce and utilities allowed them to live comfortably on a single income for years, although the cost of dining out was comparable to the US.
While they missed the convenience of American fast-food options, Jason reflects that before the move, he relied heavily on quick, processed meals. If they’d stayed in Virginia, he says he would be “really unhealthy” today.
As they got over the initial hurdles, the Salesberrys began to realize they were less eager to return to the America. When the three-year mark arrived in 2020, the outbreak of the Covid-19 pandemic and subsequent global lockdowns made staying put seem like the logical choice.
“I really thought we were going back, and I was ready to go,” says Sherry, noting that there was still a part of her that was resisting life in Italy, even refusing to hang picture frames on their walls. Jason was different, she says. “I think deep down inside he’s always wanted to stay.”
But Sherry decided to embrace her new home, shifting from reliance on language apps to learning Italian and signing up for formal Italian classes. She’s now the most competent Italian speaker of the family, navigating daily interactions with a blend of vocabulary and hand gestures.
“We need to be fluent this year,” she says. “Because none of our Italian neighbors speak English, so I can’t be the only one struggling through this.”
By 2022, the family reached another major crossroads as they began contemplating a return to the US. Jason said they had been “about 50-50 on going and staying,” but a mass shooting at a Walmart in Chesapeake, Virginia, in November that year tipped the balance.
Safety factor
“I was really worried about her safety,” he says of their daughter, who is now 10 and attends an American school at the military base.
“That was kind of the big turning point.” Jason says that he knows there is also crime in Naples, but not of the same level. “You just never hear it here,” he adds. “So that’s the big thing. Safety was paramount.”
They had other problems to contend with, though. Over the course of eight years they’d experienced increasing seismic activity around the Campi Flegrei volcano, culminating in one earthquake that reached a magnitude of 4.4.
“It kind of wrecked the city,” Jason says. “So we were like, ‘We need to move.’”
Craving a quieter, more rural lifestyle away from the quake zone, they found the ideal destination in the town of Caiazzo, located north of Naples. There, they purchased a seven-bedroom, five-bathroom property surrounded by two acres of land and a historic grove of 40 olive trees — all for approximately 250,000 euros, or $285,797.
While both he and Sherry work on the military base, and hold Permesso di Soggiorno residence permits that allow them to live and work in the country long-term, Jason says spending more time with Italians is making them feel more integrated in local culture.
“You have to consciously choose to go out and learn and mingle and immerse yourself in the culture,” he says, adding that his own Italian language skills have improved considerably since the move to the countryside.
New adventure
Their days are now filled with property renovations and agricultural lessons. “We are embarking on our next great Italian adventure: learning how to maintain the land and harvest our very own olives,” says Jason, adding that they hope to have some “nice olive oil” by October.
Nearly a decade after what was supposed to be a brief, temporary stint in Italy, the Salesberry family has now closed the door on a return to the US. They’ve even added a new member to the household — a local street dog who “adopted” them. (Sadly, the family dog who came with them from Virginia has since passed away.)
“We’re here with him because he chose us,” says Sherry.
Reflecting on their experiences, Sherry says she’s noticed an increasing number of Americans trying to relocate to Italy, but cautions about following their own route of doing it blind.
“I don’t think it’s for everyone,” she says, emphasizing that it takes at least a year to adjust to the culture shock and understand the lay of the land. “But you wouldn’t know unless you tried it… When we came here, we had no idea we were going to stay, buy a house, and be here years later.”
The family hasn’t completely ruled out the possibility of returning to Virginia a few years down the line, and have held onto their home there. But they feel that Italian life suits them better and makes them happier.
“Life is very calm,” says Sherry. “And I honestly can’t see myself going back. Even though all my family is there, we’ve lived more of our time as a family here.”
The-CNN-Wire
™ & © 2026 Cable News Network, Inc., a Warner Bros. Discovery Company. All rights reserved.