Jillian Haggerty
•6/24/2026
SOUTHWEST FLORIDA, (WINK) — For more than two decades, “Cars on 5th” has been one of Naples’ signature events — drawing thousands of visitors to Naples, Florida’ Fifth Avenue South, showcasing exotic and luxury vehicles, and raising money for local charities.
But now, the future of the event is uncertain after the Naples City Council voted to deny the Naples Automotive Experience’s 2027 special event application, citing concerns about growing crowds, road closures, neighborhood impacts, public safety staffing, and overall event size. City leaders have indicated they could reconsider if organizers return later this summer with a scaled-back proposal.
The CEO of the Naples Automotive Experience, Tom O’Riordan, says uncertainty surrounding the event has created confusion for both attendees and organizers.
O’Riordan says he’s been receiving calls from people who already booked hotels and flights asking whether the 2027 event will still happen — or if they should cancel.
He says no final decision has been made as discussions with the city continue, but acknowledges that unresolved issues may require major changes or even relocation.
He also stressed the event’s long-standing charitable mission, saying it has raised significant funding for local nonprofits over the years, while also serving as a major economic driver for downtown Naples businesses.
Despite ongoing negotiations, O’Riordan says organizers are now actively exploring contingency plans — including the possibility of moving the event out of Naples if an agreement cannot be reached.
One of the early communities showing interest is Fort Myers Beach, Florida, where leaders say they are open to exploring what it would take to host an event of this scale.
Dawn Miller, owner of The Whale and founder of What’s Up FMB, says she reached out to O’Riordan shortly after learning about the city’s decision. She is now preparing a formal pitch and working with town leadership to evaluate feasibility.
Miller says bringing “Cars on 5th” to Fort Myers Beach could help boost the island’s continued recovery following Hurricane Ian, while also drawing visitors and supporting local businesses.
Fort Myers Beach Public Information Officer Abigail Eberhardt confirms town officials are in early discussions and open to exploring the idea. She says leaders would first need to review logistics, draft a special event permit, and coordinate with fire and law enforcement officials to ensure safety and compliance before any application could move forward.
She added that an event of this size would require significant planning but could have a major impact on both residents and visitors.
Some visitors already say a large-scale exotic car event could be a major draw for the area.
Travelers from Columbus, Ohio, said they would be more likely to return to Fort Myers Beach if an event like this were hosted there, pointing to both the appeal of the cars and the opportunity to see the island’s ongoing recovery firsthand.
For now, “Cars on 5th” remains in limbo as organizers continue discussions with the city of Naples. While officials have not closed the door entirely, the denial of the 2027 permit marks a significant turning point for one of Southwest Florida’s most well-known automotive events.
O’Riordan says his goal remains the same regardless of location — to keep the event alive, support its charitable mission, and continue bringing people together around a shared passion for cars.
Whether that future remains in Naples or shifts to a new community like Fort Myers Beach is still to be determined.
