Naples, Cars on 5th would talk if other reaches out 

The city of Naples said it is willing to talk with Cars on 5th about accommodating the luxe car show on Fifth Avenue South again next year. Cars on 5th representative Tom O’Riordan said he is willing to talk with the city.  

Neither plans to make the first move, however.   

Cars on 5th announced July 15 that, “at this juncture,” it will not return to Naples in 2027. The organization said the city’s proposed permit conditions would limit attendance to about 3,500 ticket holders — roughly 75% fewer than the approximately 14,000 paid attendees at this year’s event — making the show financially unworkable and unfair to its charitable beneficiary, Habitat for Humanity of Collier County. 

The city disputed that characterization in a response July 16. 

“The proposed layout would have accommodated a substantial car show while improving emergency access and reducing impacts to surrounding neighborhoods and Cambier Park facilities, consistent with the operational and public safety concerns identified by City Council,” the statement said. 

What qualifies as “substantial” remains one of the biggest points of disagreement. 

Another is security. According to city estimates, about 27,500 people attended this year’s event, but nearly half entered without paying by walking through intersections around the event. 

O’Riordan wants Fifth Avenue South closed during the six-hour show to everyone except paying attendees and employees of downtown businesses, which is legal under state statutes. Several Council members opposed the idea during the permit discussion, and the city did not include it in its proposal. 

Without tighter access controls, O’Riordan said, nonpaying visitors will continue to contribute to parking and crowding issues without supporting the fundraiser. 

Council rejected the permit for the show at its June 17 meeting because of concerns by city staff over security, parking and accessibility for emergency responders. But the longtime high-end auto show, which has been on Fifth Avenue South for 21 of its 23 years, is both a national tourism draw and a local favorite. It’s extremely popular with restaurateurs and retailers downtown; even some who say they don’t see a bump in business that day also say that visitors remember them and return. So, Council followed its vote with a directive to City Manager Gary Young to bring city staff and Cars on 5th to the table to potentially find a workable solution for both sides. 

That solution hasn't been found.

The city response to the Cars on 5th announcement offered to continue talks: “The city remains open to continued discussion and welcomes a revised application from the applicant no later than Aug. 5, 2026, for consideration by City Council on Aug. 19, 2026.” 

But O’Riordan believes the city’s restrictions, which he said he wasn’t given until the day of the meeting, are its final offer. If that’s the case, he said, “Why are we wasting our time?” 

The show brings nearly 750 classic, high-end and unique cars to Naples every year, and is being courted by some 16 other locations, including Fort Myers Beach, which has become a serious contender, O’Riordan said.  

“We’re not leaving because we hate you,” he said. “We’re leaving because you set parameters” that would cause the show to lose money.