For years, one February weekend in Naples has looked unlike any other.
Ferraris, Lamborghinis, Porsches, Bugattis, McLarens, vintage automobiles, collector cars, and thousands of spectators have taken over Fifth Avenue South for Cars on 5th, one of the signature events of the Naples winter season.
Now, that Naples tradition is getting a new address.
Cars on 5th is moving from Fifth Avenue South to the Bayshore Drive area for 2027. The latest announcement places the main Cars on 5th Naples Bayshore show on Saturday, February 6, 2027.
And while longtime attendees may have mixed feelings about seeing the show leave the street that gave Cars on 5th its name, the move could create an entirely different—and potentially very exciting—experience.
Because Bayshore Drive isn't simply another place to park hundreds of incredible cars.
It is becoming one of the most interesting neighborhoods in Naples.
Cars on 5th Has Become a Major Naples Tradition
It is difficult to overstate how much Cars on 5th has grown.
At the 2026 event, duPont REGISTRY Group reported more than 750 rare, exotic, and collectible automobiles on display and attendance exceeding 25,000 people. The show included everything from Bugattis, Ferraris, Lamborghinis, and Porsches to live auctions, VIP areas, special guests, and curated automotive displays.
Cars on 5th is part of the broader Naples Automotive Experience, and proceeds support Habitat for Humanity of Collier County. Habitat described the 2026 event as a weekend of automotive excellence and community support, with Cars on 5th serving as its major Fifth Avenue showcase.
For Naples residents, Cars on 5th became more than a car show.
It became part of season.
You knew the event was coming when the transporters started arriving, exotic cars appeared all over town, and Fifth Avenue began filling with vehicles that you might normally only expect to see at Monterey Car Week.
Why Is Cars on 5th Leaving Fifth Avenue South?
The move follows months of discussion about the future of the event in Downtown Naples.
In June 2026, the Naples City Council denied the show's existing 2027 event application, with safety, traffic, emergency access, and logistical concerns among the issues surrounding the event's increasingly large footprint.
Organizers ultimately announced that Cars on 5th would relocate outside Naples city limits to the Bayshore Drive corridor in Collier County.
In other words, Naples isn't losing Cars on 5th.
The show is simply moving to a different part of Naples.
And that distinction matters.
Welcome to Cars on Bayshore
The name Cars on 5th may have been born on Fifth Avenue, but the 2027 event will introduce the show to a very different streetscape.
The new setting is Bayshore Drive in East Naples, an area that has been transforming over the past several years into an eclectic mix of restaurants, arts, recreation, waterfront destinations, new residential development, and local businesses.
An independent Cars on Bayshore visitor guide reports that organizers selected the Bayshore corridor in partnership with Collier County leadership with goals that include additional spectator space, expanded hospitality, and new lifestyle programming.
That could give Cars on 5th room to evolve beyond the traditional format of simply lining cars along a downtown shopping street.
And from a local Naples perspective, the timing is fascinating.
Bayshore Drive Is Having a Moment
If you haven't spent much time on Bayshore Drive lately, you may be surprised by how much the area has changed.
Visit Naples describes the Bayshore Arts District as a revitalizing East Naples neighborhood with galleries, studios, local restaurants, creative businesses, outdoor attractions, and an increasingly active community atmosphere.
One of its best-known destinations is Celebration Park, the waterfront food-truck park that has become a popular place for casual dining, drinks, live entertainment, and gathering with friends. The district is also close to Sugden Regional Park and other outdoor recreation.
Then there is Naples Botanical Garden, located directly on Bayshore Drive at 4820 Bayshore Drive. The Garden occupies a major position at the southern end of the corridor near Thomasson Drive.
Put those pieces together and you begin to see why Cars on 5th could feel very different in its new home.
A Different Kind of Naples Car Show Experience
On Fifth Avenue South, Cars on 5th was surrounded by upscale restaurants, boutiques, galleries, and the polished atmosphere of Downtown Naples.
Bayshore has a different personality.
It is more eclectic.
More casual.
More artistic.
There are food trucks, waterfront hangouts, breweries and local restaurants, public art, tropical landscaping, parks, galleries, and creative spaces throughout the surrounding district.
That could give the 2027 show more of a festival atmosphere.
Instead of Cars on 5th being an event dropped into an established luxury shopping district, Cars on Bayshore may become part of the continuing story of a neighborhood that is still being created.
And that is what makes this move particularly interesting.
Will It Still Feel Like Cars on 5th?
That's probably the biggest question longtime attendees will have.
Fifth Avenue South was undeniably part of the magic.
Seeing a line of Ferraris against the palm trees and architecture of Downtown Naples became one of the event's signature images.
The 2026 show demonstrated just how substantial the event had become, drawing more than 25,000 attendees and displaying more than 750 automobiles according to duPont REGISTRY.
Moving something of that scale inevitably changes the experience.
But different doesn't necessarily mean worse.
More space could allow organizers to rethink how cars are displayed, where VIP areas are located, how vendors participate, and how spectators move through the event.
The Bayshore setting could also expose visitors to a part of Naples they might otherwise never explore.
For thousands of seasonal residents and visitors who know Fifth Avenue, Third Street South, Mercato, and the beaches extremely well, Cars on 5th may become their introduction to the Bayshore Arts District.
That's a pretty significant opportunity for the neighborhood.
What the Move Could Mean for Bayshore Drive
From a real estate perspective, this may be one of the more interesting parts of the story.
Bayshore has already been changing.
New residential development, improvements to public spaces, restaurants, arts-oriented businesses, Naples Botanical Garden, Celebration Park, and other attractions have steadily changed perceptions of this East Naples corridor. Visit Naples now describes Bayshore as an increasingly vibrant district and a destination in its own right.
Naples Botanical Garden also reported in early 2026 on a new pedestrian connection being developed between the Bayshore District and Sugden Regional Park, another example of investment in the area's walkability and recreational network.
Now imagine adding one of Naples' largest annual lifestyle events.
Thousands of people who may have rarely ventured down Bayshore Drive could suddenly find themselves walking the neighborhood, discovering restaurants, seeing new construction, visiting local businesses, and experiencing a completely different side of Naples.
That kind of exposure matters.
Bayshore Is Not Trying to Be Fifth Avenue—and That's Okay
One of the mistakes people might make is judging the new Cars on 5th venue entirely by how closely it recreates the old one.
It won't.
And perhaps it shouldn't.
Fifth Avenue South is Fifth Avenue South.
Bayshore is becoming something entirely different.
The appeal of the Bayshore Arts District comes from its combination of old and new Naples, waterfront recreation, independent restaurants, art, tropical landscaping, residential redevelopment, and a slightly less polished—but increasingly interesting—energy.
Bringing a world-class automotive event into that environment could create an experience that feels less like reproducing Cars on 5th and more like starting its next chapter.
What We Know About Cars on 5th Naples Bayshore 2027
The main show is currently announced for Saturday, February 6, 2027, on the Bayshore Drive corridor. The broader Naples Automotive Experience is expected to include associated automotive events during the surrounding days.
Parking plans, shuttle routes, spectator access, detailed site layouts, ticket information, and other event logistics are still evolving.
There is also an important website discrepancy worth noting as of August 2026: the Naples Automotive Experience's main event webpage still displays older language identifying Fifth Avenue South as the 2027 Concours location, while the event's more recent social announcement and local reporting confirm the move to Bayshore Drive.
For that reason, anyone planning to attend should watch for updated official event information as February approaches.
duPont REGISTRY and the Naples Automotive Experience
The involvement of duPont REGISTRY Group has helped push the Naples automotive weekend further into the luxury-car world.
For the 2026 edition, duPont REGISTRY described itself as proudly hosting Cars on 5th within its growing events portfolio. The weekend included the duPont REGISTRY Village, rare and exotic vehicle displays, special guests, VIP hospitality, and a duPont REGISTRY LIVE auction.
That combination of automobiles, luxury lifestyle, collectors, entertainment, and hospitality gives the show an identity that extends far beyond a traditional local car gathering.
The question for 2027 is how that experience evolves when it has a much larger and very different Naples neighborhood as its backdrop.
Is Cars on Bayshore Good for Naples?
Change is always complicated when it involves a tradition people love.
Cars on 5th spent more than two decades building an identity around Downtown Naples. There will understandably be people who miss seeing the cars on Fifth Avenue South.
But the move also creates an opportunity.
The event remains in the Naples area.
Habitat for Humanity of Collier County remains connected to the Naples Automotive Experience's charitable mission.
The cars remain extraordinary.
And now one of the most rapidly evolving parts of Naples gets a chance to host tens of thousands of people who may never have experienced Bayshore Drive before.
It may take a year or two before we know exactly what Cars on 5th's new identity will become.
But one thing seems certain:
February 2027 is going to put a lot more eyes on Bayshore Drive.
And if you've been watching the transformation of East Naples, that's a story worth following.
Thinking About Living Near the Bayshore Arts District?
The Bayshore area is changing quickly, with new development, waterfront destinations, restaurants, arts and entertainment, and major attractions such as Naples Botanical Garden continuing to reshape this part of East Naples.
If Cars on 5th's move has you curious about Bayshore Drive real estate, East Naples homes and condos, new construction, or investment opportunities near the Bayshore Arts District, I'd be happy to help you explore what's happening in the neighborhood.
Whether you're looking for a seasonal home, full-time Naples residence, investment property, or simply want to understand where Naples is growing next, local knowledge can make all the difference.
Contact me today for a customized Naples real estate search.
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