Joy Ride: Da Maui Sleigh

A father-son holiday tradition rolls on.

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Story by Sarah Ruppenthal

maui sleigh
James Presbitero is the driving force behind Da Maui Sleigh . . . and Mr. and Mrs. Claus are two of his biggest fans.

On a balmy December evening twenty-one years ago, James Presbitero saw something unusual pass his grandmother’s Central Maui home: a pickup truck towing a small trailer-turned-sleigh. His interest piqued, he recruited his father, Kalani, to help him cobble together a sleigh atop a utility trailer hitched to Kalani’s truck. They used what they could find: two pieces of plywood, a can of red paint, and twinkling string lights plugged into the truck’s cigarette lighter.

In the nights that followed, family and friends piled into the “sleigh” and cruised the neighborhood. After Christmas, James and Kalani dismantled it, but rebuilt it the next year. And the year after that.

The father-son project became a Christmastime fixture. At dusk, kids lingered, waiting, and on spotting the sleigh, would give chase, pleading for a ride.

Before Kalani passed away in 2011, he asked James to carry on the tradition. “He saw how much joy it brought to others.” James decided to bring “Da Maui Sleigh” to other neighborhoods. He posted a self-produced video on Facebook, and within minutes, his phone started to ring and emails began flooding his inbox.

Since then, he has racked up more miles—and smiles—than he can count. He puts his landscaping business on hold most of December and hits the road with Santa, a gaggle of elves, Sandy the Snowman, and a puppet named Wilson. From morning to night, they give free rides to hundreds of passengers of all ages at “Santa Stops” in neighborhoods and at schools, churches, nursing homes, and charitable organizations all over Maui. 

Donation-fueled, volunteer-powered, Da Maui Sleigh is an in-demand holiday staple. And it’s impossible to miss: Apart from its flashing neon lights, subwoofer speakers, and glee-inducing bubble and snow machines, the no-horse open sleigh is decked out in graphics whose theme changes every year (past themes include Dr. Seuss’s How the Grinch Stole Christmas and Disney’s Moana and Frozen).

James says the rewards are immeasurable. “I can put someone in a four-by-eight trailer with bubbles and Christmas music and give them five minutes of pure joy. That’s why I do it every year . . . and why I’ll keep doing it for as long as I can.”   

Learn more—like how to get Da Maui Sleigh to visit your neighborhood or event—at DaMauiSleigh.com.

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