Cars on 5th likely to move from Fifth Avenue South to Bayshore Drive 

Cars on 5th has likely found a new home on Bayshore Drive and a show date, Feb. 6, 2027.

The organization hasn’t filed its permit applications yet, according to Mike McNees, Collier County executive director of redevelopment and facilities, to whom the Bayshore-Gateway Triangle Community Redevelopment Agency reports. However, the show’s promoters have been talking with staff members and the Collier County Sheriff’s Office about staging it on Bayshore, he added.

McNees said the permit application could go straight to the Collier County Board of Commissioners, the final authority as the executive committee for the CRA. The invitation to Cars on 5th to consider a county venue was extended through Board Chairman Dan Kowal, and the CRA Advisory Board is on a summer hiatus.

The move would end a 21-year history of staging the show on Fifth Avenue South, the street that gave Cars on 5th its name. The show had become one of the top two annual attractions on the avenue, drawing some 700 to 750 antique, rare and high-end automobiles and 14,000 paying customers. It also brought millions of dollars to local charities, including its 2026 beneficiary, Habitat for Humanity.

The show’s organizers and the city had been at odds for possibly the last five years because gate crashers were swelling the crowds to an estimated 35,000 and creating parking and security problems around downtown Naples. This summer, Naples mandated heavy restrictions on admission for Cars on 5th — limiting it to fewer than 4,000 entries — as a requirement for approving a permit for the event. Tom O’Riordan, Cars on 5th organizer, said those limits would make the show a money loser and were unenforceable without also closing Fifth Avenue sidewalks to all but paid attendees.

Several City Council members said they would not support closing access to the avenue for the six-hour show, and organizers began investigating other locations.

If approved as current planning indicates, next year’s show would close only the northbound side of Bayshore Drive, allowing neighborhood traffic and emergency vehicles access via the southbound lanes. The show area would be closed off by French barricades to keep gate crashers to a minimum.

“We’ve got some work to do because it’s a change, but I think ultimately the county — under the commissioners, the sheriff, fire department, everyone — has been just amazing to talk through the thing, to talk to the issues, supportive, and are all determined to make this thing work,” O’Riordan said. He said an application for the permit was “in the pipeline.”

The annual high-end receptions and auctions built around the show will continue at other locations on Feb. 4 and 5. O’Riordan said the recipient charity, which often helps staff the show with volunteers, would be named shortly. He also said he is working with restaurants on Fifth Avenue South that may want to offer food in the planned food court; those are among the businesses that profited heavily from Cars on 5th’s presence.

O’Riordan said there may be more innovations with the new location, which, for starters, will offer a larger VIP area. But he is still working to complete the plans. Free parking and shuttle options have already increased to include the USOP National Pickleball Center in Thomasson Park as well as the county government center.

Told the city’s Business Improvement District might court a replacement car show for Fifth Avenue South, O’Riordan said, “I wish them well.”