Driving It Forward: Tom O’Riordan on Cars on 5th and the Naples Automotive Experience

In Naples, Florida, car culture drives far more than just stimulating conversation. It powers the community, fills calendars, and raises millions of dollars for local causes. Just ask Tom O’Riordan—president of the Naples chapter of the Ferrari Club and the driving force behind the Naples Automotive Experience—who’s watched this scene grow into something truly special.

The Making of a Community

“It’s a unique community in that it’s fairly well off. People have money to spend,” Tom says. “The climate adds to that.” With eight months of dry weather, collector cars get road time, not storage time. Add a calendar full of events and a deep bench of car clubs, and you’ve got a car collector’s version of paradise. 

And those local clubs have numbers to match. The Corvette Club boasts around 600 members. The Naples chapter of the Ferrari Club has about 500—“probably the highest concentration per capita in the United States.”

“It’s hard to say exactly how [the car culture here] evolved,” Tom admits, “but I think it has to do with people going back and restoring cars they saw when they were young. People aspired to have a certain car, and by the time they move to Naples, they have the disposable income to have that car.”

From Side Street to Center Stage

Cars on 5th wasn’t always the anchor event it is today. “We started pretty small. In 2004, we had 20 cars,” Tom says. “I wasn’t involved in the show, but I happened to stumble upon it.” Since then, he’s helped shape it into what duPont Registry now calls “the best one-day show in America.”

“This past year, we had 750 cars, 30,000 attendees, 150 vendors, and raised $2.95 million for charity,” he says. “It’s come a long way in 20 years or so.”

Held the first weekend in February on 5th Avenue South—one of Naples’ most iconic shopping and dining streets—the event is a logistical feat. “We start setting up at 5 in the morning so we can have everyone in place by 8. It’s quite an orchestra to get 750 cars and 150 vendors in,” Tom says. “We measure out every inch of the street to make sure everything fits.”

An Experience That Keeps Evolving

While Cars on 5th is the centerpiece, it’s far from a one-note event. “We always try to freshen it up each year, add some new event that makes it special.” Past years have included launches from the Shelby Owners Group and a 34-car showing from the Ford GT group.

There’s also a ticketed VIP section—what Tom describes as a solution to a very good problem. “One of the challenges we ran into was getting some of the most valuable cars, especially Ferraris, on the street with that many people. I had a car last year this guy had turned down 88 million dollars for. So I had this vision a few years ago to create this VIP area.”

That vision is now a 40,000-square-foot enclosed area with full catering, wine tastings, a full bar, and room for high-end cars to be shown with a little extra breathing room.

In addition to the show itself, Tom has helped launch a JetPort reception at Naples Airport—an evening event where sponsors and guests can meet, mingle, and admire cars and aircraft. “Jay Leno came to it last year,” he says. “It’s a great place for sponsors to entertain their customers.”

A women’s event at Vineyards Country Club and a growing lineup of luxury programming have turned what began as a one-day celebration of cars into a week worth planning around.
 

Driven by Charity, Built on Camaraderie

“For a long time, until we connected with St. Matthew’s House, I kept saying, ‘we should be able to raise a lot more money,’” Tom says. That connection brought in hundreds of volunteers and made Cars on 5th a major fundraising engine. “St. Matthew’s House provides 400–450 volunteers every year who want to raise money and love the show.”

Now, they’re expanding again. Starting in 2026, Habitat for Humanity of Collier County will become the new charity partner. “They build a hundred homes a year in Collier County. Affordable housing is the number one issue here.”

“What drives me is it’s for charity,” Tom says. “At the end of the day, all of our members and other clubs—they do it because it’s a chance to meet similar people with similar interests and raise money for charity. The first thing they want to know as soon as they’re done is ‘how much have we raised?’”

The Ferrari Factor—and Naples Itself

Tom’s love of cars began early. “My brother had an Alfa Romeo. He’s seven years older than I am. I admired those, I thought those cars were beautiful,” he recalls. “My brothers were pretty crafty—they convinced my mother that a good family car would be a Mustang. So that was my first car.”

He’s been around Ferraris long enough to develop a point of view. “One of my friends is a Porsche guy and a Ferrari guy, and he says, ‘Porsches are great cars, but Ferraris have a soul.’ There’s something about Ferraris...they’re always beautiful. Ferrari has gotten it right since 1947.”

As for Naples itself? “Naples is unique in that it’s not people who are showing off—they want to get together because they have something in common. It’s just people who enjoy getting together and talking about cars.”

For Tom, it all comes back to what fuels this community: a passion for cars and the people who love them. Whether it’s a Ferrari on 5th Avenue or a Mustang from your youth, every car has a story—and Naples is where people come to share them.

For a place where car lovers all come together for something bigger, ONLY Paradise will do.