After months of uncertainty, organizers have announced a new venue for Cars on 5th.
While it will no longer be on Fifth Avenue South, its namesake street in downtown Naples, or in the city, the popular charity car-centric event isn’t moving far.
In 2027, it will be on Bayshore Drive, not far from city limits, in East Naples. It has been scheduled for Feb. 4-6.
In a news release announcing the new location, organizers said it marks a “transformative moment in the event’s evolution” and opens up “unprecedented opportunities to expand and enhance what the event delivers to automotive enthusiasts, collectors, sponsors and the Naples community.”
The event will become known as Cars on 5th Naples Bayshore.
“We are going to keep the brand; it’s a good name, and we are not far off from it,” said Tom O’Riordan, the CEO of Naples Automotive Experience, the organizers behind the event.
The search for a new location came after Naples City Council rejected the permit for the 2027 event on Fifth Avenue South, citing safety and parking concerns, and city staff and organizers failed to reach a compromise.
In a statement, O’Riordan emphasized that the move represents more than a change of venue.
“This move represents the natural evolution of Cars on 5th,” he said. “Naples Bayshore Drive gives us the canvas to build something truly special. We’re creating a destination experience that honors our automotive heritage while introducing new dimensions of programming, hospitality, and community engagement. Our collectors, sponsors, and guests will experience Cars on 5th in entirely new ways.”
The expanded location, he said, will allow for the introduction of what’s described as “meaningful innovations,” including enhanced automotive showcases, curated cultural and fashion programming, exclusive sponsorship and networking opportunities, and a broader range of attractions designed to appeal to serious collectors and lifestyle enthusiasts alike.
Since Bayshore Drive is in the unincorporated area, it required support from Collier County’s leadership.
After working closely with county leaders, the organizers felt they found a location that “provides room for growth while maintaining the intimate, curated experience that defines the event.”
In O’Riordan’s eyes, the partnership with the county underscores the event’s “importance to the Naples community and the region’s commitment to positioning itself as a destination for world-class automotive and lifestyle events.”
The event had been held on Fifth Avenue South for more than 20 years, but city council felt it had grown too big and no longer fit the street, creating too many traffic, safety and logistical issues and headaches.
After council rejected the 2027 permit, city staff proposed scaling back the event, but the organizers spurned the plan, which would have reduced the attendance by more than 75% and the footprint by about 70%.
More about the talks with county leaders
Collier Commissioner Rick LoCastro was on his honeymoon in Italy when O’Riordan first contacted him in June about the potential of having the event elsewhere in the county.
“We had positive conversations, and I connected him with senior county department leaders across the board to see what might be possible and what county location would make the most sense,” LoCastro said in an email. “He was NOT looking to have a ‘car show’ in a big giant parking lot at our Sports Complex, Coastland mall, or at the Hertz Arena … locations some citizens were recommending.”
Bayshore Drive emerged early as the “likely choice,” LoCastro said.
“We’ve known that has been the location for quite some time … but we were working through the logistics, the safety requirements, security, access, and all the support needed to make it a successful event,” he said.
For well over a month, he said, he had almost daily conversations with O’Riordan to work on the details.
“The county is excited to retain this 20-plus year tradition, phenomenal car event, and fundraiser here in Naples — this time supported by our county team,” LoCastro said. “Senior county leaders, fire, sheriff, EMS, and all the personnel needed to support this community event are working hard and leaning forward to assist in showcasing Bayshore Drive for our citizens and visitors with amazing cars, food, and a few new added surprises.”
The finer details must still be ironed out, and the county must still approve a permit for the event, but O’Riordan doesn’t see any big hurdles ahead.
He considered other locations in the county, including the Paradise Coast Sports Complex and the North Collier Regional Park, and sites elsewhere in Southwest Florida and beyond, before choosing Bayshore Drive.
“Bayshore is going through massive redevelopment,” O’Riordan said. “So directionally, it’s also good. I think we can also help businesses there and bring some more attention to Bayshore.”
More about the 2027 event
Here are some of the details that have been worked out for the 2027 event: On Feb. 5, a reception will be held at the Naples Jetport, with a fashion show scheduled for the same day — at a location off Bayshore Drive.
The main event will follow on Feb. 6 inside a fenced area off Bayshore Drive, with attendance restricted to ticket holders.
“Everybody in the county has really stepped up to figure out how we are going to do it,” O’Riordan said. “It’s pretty exciting. There are things we can do here that we could never do in the city of Naples.”
The chosen charities are two animal shelters, the Patty Baker Humane Society Naples and Collier County Domestic Animal Services. There will be a two-day Walk in the Park pet adoption event to take advantage of the crowds generated by the car show.
While the number isn’t final, O’Riordan expects to sell 14,000 to 15,000 wristbands for the event.
In response to the move to Bayshore, Naples City Councilman Bill Kramer, said: “I think it is terrific that the Cars on 5th event is staying in Collier County and I hope the new venue is the perfect fit.”
At a Collier County Tourist Development Council meeting in July, Kramer ― a member of the tourism advisory committee ― reiterated the city’s position on the event, saying he knew of several people who couldn’t get to the hospital or even be reached by first responders in their time of need because of the crowds generated by Cars on 5th in the past.
“Our first responsibility is health, health and safety for citizens, period,” he said. “And so, I say that to say our liability for the event was untenable.”
He said he could have supported a smaller event, but O’Riordan couldn’t come up with an acceptable way to host one.
In a statement, the city said it “recognizes and values the longstanding history of Cars on 5th and remains committed to supporting special events in order to provide entertainment and economic opportunities while maintaining a strong focus on public safety for visitors, businesses, and residents.”
For more than two decades, Cars on 5th has turned Fifth Avenue South into a giant luxury-car showroom, packed with Ferraris, Porsches, Corvettes, Lamborghinis, Maseratis and other heart-stopping, head-turning performance models.
This year’s event — the 22nd annual — featured more than 750 vehicles, including a strong showing of vintage, classic and antique automobiles.
More about the impact of the move
There have been talks of the Fifth Avenue South Business Improvement District (BID) putting on a car show of its own, or hosting a different type of event, on the street next year to make up for the lost revenue from Cars on 5th. The mission of the BID, which represents more than 200 businesses and property owners on the street, is to promote and market the city’s main street.
Meg Stepanian, the BID’s executive director, said: “It’s our goal to lift up the merchants. We are looking at a lot of things to do that.”
She acknowledged that Naples is about cars and wine, and Cars on 5th has been one of the most successful events on the street. However, she said, the BID knows how to put on events, with its two-day Christmas event drawing an even bigger crowd than the car show.
For the city, what’s most important is to do what’s best for the community, she said.
“It really needs to be about what the community needs overall,” Stepanian said. “So, that’s what we’re going to stay focused on.”
She added: “Our sandbox is only so big. We all have to work together to enjoy it.”
In an email, Monique Barnhart-Tiberio, the city’s public information officer, confirmed that BID submitted a new special event application on Aug. 6, but did not elaborate on the request, saying only that city council would consider it at a “future meeting.”
More car shows announced and in the works
Last week, the Cars on 5th organizers confirmed a second show will be held in St. Petersburg.
The event there will have the same Cars on 5th branding, as it will be held on Fifth Avenue and Bayshore Drive, downtown, along the waterfront, near Vinoy Park.
Meanwhile, O’Riordan continues to explore other opportunities to expand upon the original event, including bringing a smaller one to neighboring Lee County — to the town of Fort Myers Beach. Talks have gone well, said Abigail Eberhart, the town public information officer, who said she expects the event to be a go.
“It will be called Cars off Fifth, and it will be a fun, funky version, likely in December,” she said.
Asked about the event on Fort Myers Beach, O’Riordan said he planned to do one, but didn’t confirm the details.
“I’m going to do something with them,” he said. “I just don’t know when yet.”
He is also working on a smaller event at the Four Seasons Resort in Naples, planned for later this year, involving 125 cars.
“I’ve just been waiting for the golf course to reopen,” he said. “The December event is planned for the amenities area across from the hotel.”
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Laura Layden is a business and government reporter. Reach her by email at laura.layden@naplesnews.com.
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This article originally appeared on Naples Daily News: ‘Cars on 5th’ finds new home after city permit denial
Reporting by Laura Layden, Fort Myers News-Press & Naples Daily News / Naples Daily News
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By Laura Layden, Fort Myers News-Press & Naples Daily News | USA TODAY Network
