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Ross Klein, president of Starwood’s Luxury Brands Group, puts as much care into his cars as into his hotels.

It’s fitting that Ross Klein, the president of Starwood’s Luxury Brands Group, would drive one of the most luxurious of all sets of wheels on the road: a Tungsten 2007 Bentley Continental Flying Spur. “I love the Flying Spur for its precision and tossability,” Klein says. “It was perfect for my ambition to have a car from the classic era, but it also addressed the logistics of being in a metropolis. It has the craft of a ’30s and ’40s [Rolls-Royce] Phantom but the intelligence of a modern car.”

Klein’s love for cars began just a few years after he learned to talk. “I’ve been an enthusiast since I was six,” says the executive, who oversees the international collection of luxury hotels that includes the W and St. Regis brands, as well as properties such as Venice’s opulent Hotel Gritti Palace. And he has owned a car since before he could legally drive.

“My first was a 1967 Cadillac Fleetwood that had belonged to my uncle. My parents paid $200 for it and I cut yards and cleaned a gas station to pay them back. I was 13 and wasn’t old enough to take it out on the road, so I drove it up and down the driveway.” The current tally stands at more than 75 cars over his 45 years, including the seven in his current collection, which he keeps in New York and Florida.

Despite maintaining a grueling schedule, the Manhattanite sees to the loving care of his cars himself, with a little help from his friends. “For me, you don’t know your car until you’ve caressed every inch of it,” he says. “Washing them is a therapy. Everyone at my house in Florida on weekends gets a sponge and a hose, and we all have a car wash.”

Klein sees parallels between the experience of owning luxury cars and the high level of service provided to guests at the five-diamond properties he oversees. “Even our ‘Wheels’ program at the W offers everything from green transportation to an S.U.V. at your service,” he points out. “In regard to my driving personality and business personality, my team would probably say the parallel would be speed! My personal style is to try to get to the destination with prudent speed and enjoy the journey.”

Enjoying means taking out each of his cars at least once a month; he is also happy to hand the keys over to friends. “If I’m out over the weekend, I’ll take my Jaguar E-type to the gym,” he says. “For a little speed, I take the Flying Spur. I have a Continental GT, but the hard part of that is that everyone wants to ride and [it only fits two comfortably]. You want to share the experience, and I can share the Flying Spur with three or more friends.”

“People say, ‘A new Bentley? What does that set you back?’ But it’s a value statement. Would you rather have 10 shirts off the rack or a bespoke shirt? If you’re gonna buy a car every four to five years and you have, say, 40 years to go in your life, why not just get a bespoke, limited-production model?”

He’s not blind to the charms of other luxury automobiles—like his Curzon-blue 2004 Rolls-Royce Centenary Phantom.

“Visually, there isn’t anything like it out there,” he says. “It’s not that they’re retro—they’re truly classic. Both cars are totally true to their original authenticity, no expense spared, and aimed at connoisseurs of the drive. The Phantom guys are using Rolls’ initial mission statement: ‘Take the best that exists and make it better. When it does not exist, design it. Strive for perfection in everything you do.’ That car now is an homage to all the principles the founders had, and a treat for the drivers.”

Collecting cars doesn’t mean one has to spend a fortune, according to Klein. In his collection is a 1991 Cadillac Allanté, for which he paid just $3,500. “It was Cadillac’s first venture into the luxury-car market,” he explains. “They believed in the product so much that they even guaranteed the resale value of it against Mercedes. It was a marketing and design debacle. But as a curiosity, it’s an amazing car. When I was at Pebble Beach this year, there was a section of Allantés in the middle of all these $2 million collections of Ferraris and Lambos.”

And what does his collection say about him? “I think people say, ‘Here’s a guy who loves cars,’ ” he opines. “They’re part of our cultural wardrobing. People buy them to accessorize themselves, and it’s an art form. If they ever take away my keys, my life will be over.”