Cars on 5th Is Moving to Bayshore: What It Means for Naples

For more than two decades, one of Naples' most recognizable annual events has been practically synonymous with its address. Cars on 5th filled Fifth Avenue South with Ferraris, Porsches, Lamborghinis, Corvettes, classics and other extraordinary automobiles, attracting thousands of spectators to downtown Naples.

In 2027, however, the cars are getting a new address.

Cars on 5th is moving from Fifth Avenue South to the Bayshore Drive area in East Naples. The name may take a little getting used to in its new surroundings, but the move is significant for more than car enthusiasts. It brings one of Naples' best-known events to an area that has been steadily developing an identity of its own.

And if you have been following what is happening along Bayshore lately, the timing is particularly interesting.

First, What Is Cars on 5th?

If you've never experienced Cars on 5th, calling it a "car show" doesn't quite capture it.

The event is part of the larger Naples Automotive Experience and has become a major annual gathering for collectors, automotive enthusiasts and people who simply enjoy seeing some spectacular cars. Expect everything from exotic and modern performance cars to vintage automobiles, prototypes and collector vehicles.

For 2027, the Naples Automotive Experience is scheduled for February 4 through February 7, with the primary Cars on 5th show taking place Saturday, February 6.

The four-day lineup begins with a Jay Leno Charity Comedy Night at Hertz Arena on Thursday. Friday brings the JetPort Reception at Naples Airport, combining supercars and luxury aircraft with food and cocktails. Saturday is the main automotive showcase on Bayshore Drive, followed by an after-party, and the weekend concludes Sunday with Rally for Heroes.

Proceeds from the event benefit the Patty Baker Humane Society of Naples.

So while the Saturday car show gets most of the attention, this has evolved into a much broader Naples automotive weekend.

Why Is Cars on 5th Leaving Fifth Avenue?

The move follows months of discussion between event organizers and the City of Naples regarding the future of the show downtown.

Naples City Council ultimately denied the event's 2027 permit application, with concerns that included safety, parking and the logistics involved in accommodating such a large crowd in the downtown environment. Event organizers and the city were unable to reach an agreement on a revised format that worked for both sides.

Rather than ending the event or moving it out of the Naples area altogether, organizers found a new home just outside the Naples city limits along Bayshore Drive.

That is where the story gets particularly interesting.

What Will Cars on 5th Look Like on Bayshore?

It will certainly look different.

The main Saturday show is expected to occupy the northbound lanes of Bayshore Drive, with hundreds of vehicles displayed along the corridor. Current plans call for cars to stretch from the Weeks Avenue area south toward Thomasson Drive.

That creates a very different environment from Fifth Avenue.

Instead of fitting the show into Naples' established downtown streetscape, organizers have a larger canvas to work with. Plans include new display areas, a dedicated VIP section, the duPont REGISTRY Village, vendors, restaurants and transportation options to help visitors navigate the event.

One familiar tradition is also expected to survive the move: the End of Show Drive-Off, when spectators get the chance to watch and hear many of those beautiful cars actually leave under their own power.

Organizers have also said ticket sales will be limited in 2027, an intentional effort to reduce crowd density and make it easier for attendees to actually see and enjoy the cars.

For anyone who has attended Cars on 5th on one of its busiest years, a little extra elbow room probably won't be terribly controversial.

Parking Could Actually Be One of the Interesting Changes

Moving an event this large inevitably raises the question: where is everyone going to park?

The current event information lists several parking and shuttle locations, including the Collier County Government Complex, the USOP National Pickleball Center and Sugden Regional Park. Those locations surround the Bayshore area rather than concentrating vehicles in one downtown parking environment.

That could fundamentally change how people arrive at the event.

Instead of everyone attempting to park as close as possible to the show, the model appears designed to move people into the district from several surrounding locations.

As we get closer to February, anyone attending should check the official event information for final parking, shuttle and traffic plans because details can still change.

And Then There Is Bayshore Itself

This may be the most interesting part of the move.

Bayshore isn't Fifth Avenue, and I don't think it should try to be.

Fifth Avenue South has its polished downtown atmosphere, restaurants, shops, hotels and established luxury identity. That setting was unquestionably part of the Cars on 5th experience for many years.

Bayshore has a very different personality.

It is home to Naples Botanical Garden, Celebration Park, Rebecca's, Ankrolab Brewing Company, restaurants, galleries and locally owned businesses. Nearby are Sugden Regional Park and the USOP National Pickleball Center at East Naples Community Park.

And now, as I recently wrote about, the new Bayshore-to-Sugden pedestrian boardwalk creates another connection between Bayshore Drive and one of East Naples' major recreational spaces.

Put all of those pieces together and something interesting is happening.

Bayshore is increasingly becoming a place where people don't simply drive through. They come to eat, walk, bike, visit the Botanical Garden, play pickleball, attend events and spend part of their day.

Bringing Cars on 5th here could introduce thousands of people to that version of Bayshore.

What Could This Mean for Bayshore Businesses?

Potentially, quite a bit.

A large destination event creates foot traffic, and foot traffic creates opportunities for nearby restaurants and businesses. But perhaps the bigger benefit is exposure.

There will undoubtedly be people attending Cars on 5th in 2027 who know Fifth Avenue extremely well but haven't spent much time exploring Bayshore.

They may arrive for the Ferraris and discover a restaurant they want to revisit. They may notice Naples Botanical Garden. They may discover Celebration Park or a local business they didn't know existed.

That kind of exposure can matter long after the last Lamborghini drives away.

There will also be tradeoffs. A major event means road closures, traffic, crowds and disruption for nearby residents and businesses. How effectively those logistics are managed will be an important part of judging the move after the first year.

But from a neighborhood-development perspective, having one of Naples' signature events choose Bayshore is noteworthy.

Does This Change the Character of Cars on 5th?

Almost certainly.

Whether that's a positive or negative will probably depend on what you loved about the original event.

If part of the magic was seeing exotic cars lining historic Fifth Avenue with downtown restaurants and storefronts as the backdrop, that experience can't simply be recreated somewhere else.

But Bayshore offers something Fifth Avenue couldn't easily provide: room to rethink the event.

Organizers are describing the move as an opportunity to expand the experience beyond automobiles with additional hospitality, cultural and lifestyle programming. The new setting also provides more flexibility for displays, transportation and crowd management.

The first year will be the real test.

There will undoubtedly be things that work beautifully and things that need tweaking. That's fairly normal when an event that has occupied the same environment for more than 20 years suddenly moves somewhere completely different.

Personally, I think comparing the new show to the old one detail by detail may miss the point.

This isn't Cars on 5th trying to recreate Fifth Avenue on Bayshore Drive. It is an opportunity to create a different experience.

Another Sign of Bayshore's Evolution

From a real estate perspective, I pay attention to changes like this because neighborhoods aren't shaped solely by houses and sales statistics.

They're shaped by investment, infrastructure, businesses, recreation and the reasons people choose to spend time there.

No single event transforms a neighborhood, just as no single boardwalk or restaurant does. But when multiple things begin happening in the same place, a broader pattern can emerge.

The new Bayshore-to-Sugden connection, Naples Botanical Garden, the USOP National Pickleball Center, Sugden Regional Park, new businesses and restaurants, and now the arrival of one of Naples' largest annual events are all bringing attention to this part of East Naples.

Cars on 5th moving to Bayshore is another fairly big piece of that puzzle.

So, Is It Still "Cars on 5th"?

Apparently so, at least for now.

The organizers continue to use the familiar Cars on 5th name, sometimes paired with "Naples Bayshore." After more than 20 years, the name has become a brand in its own right.

There is admittedly something wonderfully Naples about an event called Cars on 5th taking place nowhere near Fifth Avenue.

But perhaps that's also a sign of just how established the event has become.

The cars are moving. The tradition isn't.

And on February 6, 2027, we will get our first real look at what happens when one of Naples' most established events meets one of its most rapidly evolving districts.

I have a feeling Bayshore is going to look pretty good with a few Ferraris parked along it.

2027 Naples Automotive Experience at a Glance

February 4: Jay Leno Charity Comedy Night, Hertz Arena
February 5: JetPort Reception, Naples Airport
February 6: Cars on 5th Naples Bayshore, main automotive showcase
February 7: Rally for Heroes

Event details, parking arrangements and programming may change as plans are finalized. Check the official Naples Automotive Experience information before attending.