Robert Gaglio moved to Florida's sunny Gulf Coast in 2005, worked as a banker, owned his house and put money aside to fund his children’s education. Come 2008, the bank he worked for collapsed and he lost his job. Depression, divorce and a family crisis—dealing with mental illness with his daughter—ensued. “I did the American dream, and I got caught in a bad place,” he says. From 2008 to 2011, Gaglio put the pieces of his life back together. He got a new banking job in Sarasota, joined the YMCA and saw a therapist. About to turn 50 and watching his son graduate from high school in 2012, he decided to travel to Italy and seek out his extended family—as his parents had done in 1974 when they visited the country. Gaglio’s grandparents on his father’s side grew up in Sicily, and his mother was born there but immigrated to the United States in 1927.  

Following a family tree drawn on the back of a coupon by his father, Gaglio and his son, Tony, traveled to the small mountain town of Montelepre. There, they met Gaglio’s father’s second cousins and other relatives, who welcomed them with open arms as they ate, visited and poured over old family photo albums. One cousin, Luciana, told Gaglio that, on his next visit, he would stay with her, in the house where his parents stayed on their 1974 trip—when Luciana was eight years old. “I decided, at that point, that I was coming back to see these people as often as possible,” he adds. 

Gaglio returned to Florida, where he shared his story with his boss, Kurt Younker, a world traveler who ran with the bulls in Spain. Upon hearing that Gaglio planned to return to Italy during the same time he was traveling there, Younker invited him to stay with him and his family in a villa he had rented in Tuscany. “I think he was such a traveler that he really enjoyed my story, and he took such an interest in me,” says Gaglio. “This is why these are not coincidences. This is an angel who has been placed in my life, because I could’ve crawled into a bottle, drank, gotten more depressed and ruined my life. Instead, I was looking for life, and I think he caught that.” 

Gaglio, who had a passion for Italian food, agreed to accompany Younker and his family, as long as he could cook for them during their trip. The 2013 vacation allowed Gaglio to channel his love of cooking, but also to see how Younker traveled and hired private guides for his family instead of joining large tour groups. After the trip, Gaglio realized that he could host other travelers on all of his Italian vacations. He cooked for them, booked a villa, secured tour guides and treated them to a wonderful experience. Through his work colleagues, he booked more and more tours and quit his banking job in 2015 to start his company, Italian Culinary Tours. Today, the business coordinates tours and vacations on the Amalfi Coast, Sicily, the Dolomite Mountains and Tuscany, as well as custom and specialty tours and weddings. Stateside, the business produces Italian dinner theater and cooking classes, transporting the magic of Italy to the Gulf Coast. Eager to spread the word about his work, Gaglio taught cooking and cultural classes and conducted food tours in Sarasota. “Sometimes, there were five people in the audience,” he adds, explaining that it took an average of eight to 18 months for people to go through the sales cycle and book a tour. “I loved it. I never pretended to be an expert. I was just a guy who was really passionate about Italian food and culture and wanted to share it.” 

As he conducted business, Gaglio kept in touch with his family back in Sicily, and hosted Luciana and her son and daughter when they visited Florida for Christmas in 2013. After his divorce, Gaglio had grown accustomed to spending the holidays alone, but that year, he was among loved ones. Luciana taught him to make her tiramisu, which he has taught his clients to make. When Luciana passed away in 2017, Gaglio found himself standing with her daughter in her mom’s kitchen, asking how she was doing. “She said, ‘I’m okay, but I don’t know how to make my mom’s tiramisu,’” he adds. “And, as we made it, she said, ‘I feel my mother when I’m with you.’ When people emailed me after a class and said, ‘That was the best tiramisu I’ve ever had,’ I sent it to her.” 

While COVID shut down Gaglio’s business for two years, he used his time to write Freedom to Wander: Connecting with the Past, Reinventing the Future, a book that chronicles his 10-year journey from being a banker to an Italian tour specialist. He calls it a “story of finding family that’s been disconnected because of immigration, and of transforming your life.” Like many travelers, Gaglio would never have reached his current destination without the help of those he met along the way, like Younker and Luciana, or without the hard lessons that life taught him as he went. “If I’d gone to Sicily when the kids were little, and I had the mortgage payments and the car payments and all that stuff, maybe I wouldn’t have been so open to what I was seeing and the love that I was receiving. Maybe I would’ve been checking emails and not totally present,” he says. “But, because I was torn down the way I was, there was something about going there, that I was present and able to receive this love. They didn’t know me from Adam, I was a cousin—a distant cousin—but it didn’t matter. There was this connection immediately.”