How Chip Cunningham, "A Kid From The Midwest," Became Cliffside Beach Club's GM - And Its "Sandboni" Driver

Is this the best summer job on Nantucket?

The so-called “Sandboni” at the Cliffside Beach Club rakes the north shore beachfront every morning during the season before those signature umbrellas are planted in the sand to create one of the most picturesque backdrops on the island. Chip Cunningham has been Cliffside’s Sandboni driver for nearly 40 years, and it’s a role he still loves. Obviously.

“I'm a kid from the Midwest, and I came out here, and I'm like, ‘this is a thing? You need me to drag the beach in a Jeep in the morning?’ And many, many, many, years later, I still think it's the greatest way to start a day,” Cunningham said, sipping a cup of coffee as he makes the turns on the beach in the 1998 Jeep Wrangler.

Cunningham, who has three children with his ex-wife, the island author Elin Hilderbrand, first came to Nantucket in the late 1980s and got a job working as a bellman at the Cliffside Beach Club. He’s since worked his way up to general manager, but has kept his morning gig driving the Sandboni.

“The job is very interactive, very social all day, but this is kind of the zen way to start the day,” he said. “And also I can make sure everybody shows up on time, and think about the three or four things that need to be done today.”

Landing where’s at today was a combination of luck, hard work, and being in the right place at the right time, he said.

“I’m originally from South Bend, Indiana, but I had spent a winter skiing in Breckenridge, Colorado and my neighbor in my condo was a guy named Jeff Silva, whose family owns The Galley,” Cunningham recalled. “And we had a great winter. Skied 70 days, worked in a bar, underage of course. Don't tell my kids that. In the springtime, I was going back to Indiana to get my stuff together and figure out life, and he says ‘You think this was fun? You’ve got to come to Nantucket!’ So in 1986, I came out here and I started at Cliffside as a bellman. I showed up here about two years after they built the hotel, and just landed on my feet in a place where they needed a nice kid from the Midwest to work as derriere off. And years later, here I am still.”

The Sandboni driving is simply carrying on a tradition at the Cliffside that began long befor he arrived.

“Years before me, there was my boss, whose family has owned the property since 56 or 57,” Cunningham said. “They bought a little pickup and started doing it because he was tired of his father making him do it by hand. And so years later, I came along in the late 80s, and at that point, he had purchased the Jeep.”

The Cliffside Beach Club has 110 families that are members, and Cunningham is the leader of a crew that keeps its small slice of the north shore of Nantucket pristine during the season.

“It has to be pristine, that’s the product we offer, and it has to be nice,” he said. “At some point, I’m going to figure out what to do for a living. But until then, this is pretty good. I probably shouldn’t say this out loud, but I get up every morning and get paid to go to the beach and go to work, and that’s enough for me.”