City of Naples says 'Cars on 5th' is still welcome after organizer plans to leave

In a statement on Facebook, Cars on 5th said the city's proposed changes would have reduced the event by about 70%, eliminated vendors and dealers, increased costs and significantly changed the overall experience. The event will return to Southwest Florida in 2027 and continue to raise money for a local organization. 

WINK News spoke to business owners in the area, one said they had employees choose not to work the same day as Cars on 5th, or spent hundreds of dollars on valets to make sure their clientele could get to appointments.  

Other businesses are upset about losing foot traffic and one of their most profitable days of the year. 

Jordan Brown, managing partner of Jet Agency, said his company does about a million dollars in private jet time during the one-day event. Jet Agency had a booth at Cars on 5th years ago, and it ended up being so profitable they opened their Naples storefront. 

"From a revenue standpoint, it's the one day that justifies us having this, you know, expensive space, right?" Brown said. "You know, 5th is expensive to be on, so we'll probably leave." 

On June 17, the City Council reviewed the special event application for the 2027 Cars on 5th event but did not approve it as submitted.  

The city said the application proposed several significant changes from previous years, including expanded street-closure hours, additional road and sidewalk closures, pedestrian-access restrictions, and the implementation of an access fee for pedestrians and business patrons. 

Council also expressed concerns regarding the continued use of the Cambier Park softball fields and the condition of the facilities following the event. Instead of approving the application, Council directed O'Riordan to work with City staff to develop a revised proposal that addressed concerns regarding public safety, neighborhood impacts, traffic management, emergency access, and park use. 

On July 9, the Mayor, City Manager, Police Chief, Fire Chief, Community Services Director, and O'Riordan met to discuss alternatives consistent with the direction provided by City Council.  

City staff developed and presented an alternative event configuration utilizing the full length of 5th Avenue South from 3rd Street South to 8th Street South, along with adjacent side streets. 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 city said at that time O'Riordan did not present a revised plan or alternative proposal but instead expressed concerns regarding the direction provided by the City Council and would review the proposed configuration with his team, evaluate the event footprint, and follow up with City staff. 

O'Riordan said the city’s revised plan reduced the size of the event by 70%, allowing just 3,500 people to attend in 2027. He said that in their last meeting, he thanked them for 21 years on 5th Avenue and wished them the best. 

“ We try to be good partners,” said O’Riordan. “We're never gonna make everybody happy. Uh, we put on a really, really good event. It's world-renowned. We bring a great fun town, and we will bring them someplace else, and it's okay.” 

The City says it values the longstanding tradition of Cars on 5th and recognizes the positive impact the event has had on the community, local businesses, participating charities, and automobile enthusiasts over the past two decades. 

In 2026, Cars on 5th attracted clients from 47 states and 12 other countries. For Southwest Florida, Cars on 5this a yearly highlight. 

"This is our Mecca. This is our downtown, and we need to support it in the season and in the off-season. And that's such a big," Nicole Black said. 

Dylan Black said he likes Cars on 5th because it's something for them to look forward to in Naples. 

The shops and restaurants in downtown Naples add to the well-renowned car show that in eight years has donated $10 million to local organizations. O'Riordan said they think they've created a really good event, but it's not just about what they do—it's the other facets that really bring the show into a special night. 

 “Cars on 5th is unique; people wanna say it's just a car show. It's not. It's actually kind of a cultural event. It's considered one of the top five events in the United States. We bring great crowds into town, and so what makes it special is we, we get great cars, and we have the relationships to bring those in.” said O’Riordan. “ Ours is unique because what brings people to downtown Naples is the shopping. They come down with their wives in the morning, they go to coffee, the women shop, or spouses shop because we also have a lot of women that show cars. So it's that, and it's family, and it's the venue itself.” 

The show will go on. O'Riordan said they've trademarked the term "Cars Off 5th." 

“ I think we've made the show, the quality of the show, better every single year from the quality of the cars, the vendors, the catering,” said O’Riordan. 

After the event permit was denied, O’Riordan said thirteen venues reached out offering to be an option for Cars on 5th in 2027.

 “ It'll be in Southwest Florida,” said O’Riordan. “We've looked a couple of other venues that are nearby, a couple golf courses.” 

O’Riordan said his team has narrowed down the thirteen venues to five or six, wanting to still have restaurant and shopping options.  

 “ Downtown Naples is beautiful, but it's not the only one that we like this," said O’Riordan. “We look at other venues; we're considering all the things that we think have added to it. You know, we, we think we've created a really good event, but it, it's not just about what we do. It's, it's the other facets that really bring the show into kind of a special night.” 

O'Riordan said Cars on 5th will continue to deliver a world-class experience at its new location.