Stephanie Synclair was on her own "Eat, Pray, Love" journey in 2012 when she first visited the place that would become her second home. Synclair was newly into her entrepreneur era, having quit a 10-year corporate marketing career to become a consultant and work for herself. "I knew it was time to quit corporate America when I was sick of people telling me when to take a lunch break," she says. "I wish it was deeper than that."

Starting her own consulting business meant Synclair could work from anywhere, including while traveling the world. She looked for the cheapest flights for her first trip out of the country — "It was Palermo, Sicily, and that's how we ended up here," she tells CNBC Make It. For a roughly $250 plane ticket, Synclair set off to Sicily with her then 6-year-old son, Caden.