By Peter Barhydt
The morning air is crisp, the pavement still damp from the previous night’s rain. A thin mist lingers, curling around the black sedans lined up in meticulous rows, their hoods reflecting the first light of day. Santo Silvestro moves through them like a jeweler appraising his finest gems, his fingers brushing over the polished metal, his eyes catching imperfections that no one else would notice. He stoops to examine a tire, pressing the rubber with practiced precision. He has done this every morning for decades, before the phones start ringing, before the first car rolls out to its waiting passenger.
In the quiet of dawn, Hoyt Livery belongs to him alone.
Santo never intended to own a limousine service. He was a body man first, a mechanic with a meticulous touch, a craftsman who took pride in restoring vehicles that others would discard. In 1980, at the age of 21, he purchased New Canaan Auto Body with money he didn’t really have, scraping together every dollar, making promises he wasn’t entirely sure he could keep.
“I didn’t sleep for a year,” he says. “Every night I lay there thinking, what if I fail?”
Failure, however, never came. By the time he and his wife Lynda acquired Hoyt Livery from the Hoyt Funeral Home in 1987, Santo had already earned a reputation for precision. The limousine service had only a single stretch limousine and a silver town car—vehicles more suited for funerals than for business travelers or corporate clients.
“They thought it would be a good addition to the funeral business,” Lynda recalls. “But really, their kids just used the cars.”
The Silvestros saw potential, but the real work was in gaining trust. Santo walked into every deal with the same simple principle: If he said he would do something, he would do it. He repaired the cars meticulously, treated his drivers like family, and personally took the wheel when necessary.
“I drove for years,” he says. “Because when you’re starting out, you do everything yourself.”
Trust, in the Silvestros’ world, is not granted lightly. It is built through consistency, through showing up, through doing things the right way when no one is watching.
“We don’t lease our cars,” Santo says, shaking his head. “We own them. We maintain them.”
In an industry where most competitors lease vehicles and outsource repairs, Hoyt Livery stands apart. They own their body shop. They have their own mechanical shop. Their own car wash.
“There’s a guy whose only job is to clean cars,” Santo says. “Six days a week.”
This obsession with control extends to every detail. Every driver is an employee—never a contractor. “If Peter Barhydt calls for a car and we’re booked, we don’t hand him off to another company,” Lynda says. “If we take the job, we take responsibility.”
It is a philosophy that sets them apart in an era of ride-sharing, where Uber and Lyft have turned transportation into a nameless transaction.
“Uber drivers don’t have their cars inspected the way we do,” Lynda says. “They don’t have the same insurance requirements. They don’t get checked the way we do.”
Santo leans in. “You get into one of our cars, I can tell you that car has been checked. I know who’s behind the wheel. And if something doesn’t feel right, the driver tells us, and we pull it off the road. No questions.”
This is not a business for the passive. Santo and Lynda do not delegate from a distance. They are in the office, on the lot, at the shop—every day.
“You can’t just run it,” Santo says. “You have to live it.”
New Canaan is different now. The old way of doing business—the way Santo prefers—is fading.
“We bought 11 commercial buildings on a handshake,” Lynda says. “That doesn’t happen anymore.”
One by one, Santo acquired the lots that surrounded his growing empire: a paint shop owned by Norwalk Community College, a body shop from Modern Plumbing, a storefront from a retiring friend. Each deal was sealed with a handshake, a promise, and a mutual understanding.
“If you’re ever thinking of selling,” Santo would say, “come see me first.” And they did.
Even the deli across the street, a New Canaan institution for decades, found its way into their hands.
“The owner’s sons didn’t want it,” Santo says. “I wanted the property.”
He agreed to buy the business on the condition that he could purchase the land. Decades later, when the time came to step away from running the deli, Santo handed the business—not sold, but handed—to the two employees who had been running it for years.
“I promised them,” he says simply. “I kept my word.”
The future of Hoyt Livery is already in motion. Nicole and Anthony Silvestro, Santo and Lynda’s children, now handle much of the daily operations. They have inherited more than a business—they have inherited a philosophy.
“Our kids are our exit strategy,” Lynda says. “But we’re still here. We always will be.”
Santo smirks. “I don’t golf. I don’t like sitting still.”
Instead, he flies helicopters. He owns two Fixed Base Operations (FBOs) at Danbury Airport, selling jet fuel and renting out hangar space. It’s his escape, his way of staying busy outside the confines of Hoyt Livery.
Yet, each morning, he is back at the lot, walking past the rows of black town cars, touching the hoods, checking the tires, making sure everything is in order.
He does not do this because he has to. He does it because it is who he is.
Some men build businesses to leave them. Santo Silvestro built Hoyt Livery so he would never have to.
