If you’ve ever entered a contest to win a huge prize — a cruise, a trip, a car — the chances you’ll win usually aren’t too good.

That’s what Darrell Pistone thought when he entered to win a trip to Italy. But he was wrong.

Out of more than 280,000 applicants, Pistone, who lives in Tucson and is a retired firefighter from New York, recently won a trip to the Italian village of Grottole.

And he gets to live there, basically for free, for three months starting in June.

Before stumbling upon Airbnb’s Italian Sabbatical contest, which was created with the nonprofit Wonder Grottole, Pistone began researching his ancestry and was hoping to apply for dual citizenship in Italy.

He later found out that his grandfather is from Grottole — the same village he’ll be living in in less than a month.

“It was kind of a miracle,” he said, adding that he decided to apply for it on a whim.

When he got the good news that he was selected, he couldn’t believe it.

“I never win anything,” he said. “I was shocked and overwhelmed and it was very emotional.”

While he’s there, he’ll not only get to soak up Italian culture, but he’ll be a volunteer with Airbnb to help revitalize the village.

“It went beyond me wanting to find out where my ancestors are from — I was going to go there anyway, whether I won or not,” he said. “But then I found out they’re trying to do something to help save this village in Italy. The village is disappearing and unless they get some influx of interest in his area, these small villages are going to disappear.”

While in Italy, Pistone, in addition to four other applicants who were selected, will get lessons on the Italian language, cooking, beekeeping, gardening and farming.

The volunteers will then become Airbnb co-hosts, hosting places to stay in addition to facilitating “experiences,” which Airbnb says are unique tours and activities given to visitors.

Proceeds from the experiences will be invested back into the village, according to Airbnb.

Airbnb will cover Pistone’s lodging and travel expenses and he’ll also get a monthly stipend.

“I’m excited to meet the people and explore my roots, and maybe, perhaps, meet some relatives,” he said.

Contact reporter Gloria Knott at gknott@tucson.com or 573-4235. On Twitter: @gloriaeknott

Metro Producer

Gloria is a Tucson native and attended the University of Arizona. She started at the Star as an apprentice in 2017. Following her apprenticeship, she began freelancing until becoming a full-time reporter and producer after her college graduation in 2018.