The Jet Set with Joseph McCabe

From his much-loved hometown, an aviation enthusiast pilots business and luxury travelers through private plane ownership

Joseph McCabe stands next to his family’s Dassault Falcon 900 EX, parked in their 14,000-square-foot hangar. Photo by Nick Shirghio
Joseph McCabe stands next to his family’s Dassault Falcon 900 EX, parked in their 14,000-square-foot hangar. Photo by Nick Shirghio

Joseph McCabe occupies a front-row seat at the Naples Airport. Every day through the picture windows of his spacious corner office on Citation Point, he observes myriad planes taking off and landing on runways No. 5 and No. 23. His bird’s-eye view of the airport—better known in the skies by its three-letter geocode APF—is “definitely distracting,” he says.

Joseph McCabe. Photo by Nick Shirghio
Joseph McCabe. Photo by Nick Shirghio

If this was the Van Nuys Airport in Los Angeles County, Joseph might have the paparazzi on speed dial, sharing who was visiting or leaving town. But in Naples, a place Joseph describes as “a mecca for the rock stars of Wall Street” and a haven for those who “want to hide and not flaunt it,” he discreetly witnesses the private jet passage of business celebrities. If he spots a headliner—like Tom Cruise and his daughter taking off in Cruise’s Falcon aircraft—he merely waves. He cracks a smile at the possibility that Elton John may be aboard the jet with tail letters reading “MUSIC.”

Joseph is the eldest son of legendary Naples hotelier and developer Philip McCabe Sr., who, after serving in the air force and the CIA and owning and operating a bed and breakfast in Maine, was lured south by the weather in the early 1980s. “A conversation with some friendly folks prompted a visit to Naples and the rest is history,” recounts Joseph. The senior McCabe established McCabe’s Irish Pub on Fifth Avenue South and ran it for 16 years; he then opened the Inn on Fifth, a 119-room boutique hotel.

Born and raised in Naples, Joseph grew up in some of the town’s toniest neighborhoods, from Bay Colony to Gulf Shore Boulevard, and places in between. He attended Community School of Naples and graduated from High Point University in North Carolina in 2017 with a business administration degree, underpinned by concentrations in entrepreneurship and political science.

As a teenager, he remembers he was eager to “get out of Naples”—a place he once described as “a sleepy retirement town.” However, after his years away at college, he began to yearn for the manicured medians and sense of community he fondly associates with the coastal town. He returned and joined the family business, taking on the role of vice president of development for Gulf Coast Commercial Corporation—primarily a real estate holding company.

From his second-floor corner office, Joseph has a bird’s-eye view of the Naples Airport. Photo by Nick Shirghio
From his second-floor corner office, Joseph has a bird’s-eye view of the Naples Airport. Photo by Nick Shirghio

A Business Takes Flight

Joseph is no stranger to the world of private jet travel; family vacations included trips to Paris or the mountains of Switzerland via charter flights. The family plane was often his transportation to and from college. Although Philip McCabe Sr. served in the air force, he did not know how to fly. A purchase of a Cessna 172, later followed by an Eclipse Very Light Jet, was meant to propel him toward piloting. However, as Joseph, who tagged along on his father’s flying lessons as a young teen, remembers, “dad would end up studying the real estate from the air, while I spent the time learning about the plane.” A self-described avionics nerd, Joseph enrolled in lessons with Rexair, one of two flight schools that operate on-site at the Naples Airport. He has since amassed more than 40 hours flying solo, completing his training in October.

Because he lives in a state that reports one of the largest fleets of private jets (according to Business Airport International) and near an airport that ranks in the nation’s top 20 for busiest private jet travel (per globalair.com), Joseph was uniquely positioned to monetize his lofty hobby. In 2019 he founded Naples Jet Sales, offering concierge-level service aimed at helping clients buy the perfect plane. “Purchasing an aircraft is complicated,” he says, explaining that he has even become an expert in aviation financing.

Joseph’s entrance into the market comes at a time when the private jet industry is experiencing significant growth due to an increase in personal wealth along with the evolving needs of business travel—especially in North America, where he explains that there is “much better infrastructure to fly private versus in Europe.”

Joseph in his office’s galley kitchen. Photo by Nick Shirghio
Joseph in his office’s galley kitchen. Photo by Nick Shirghio

After the successful sale of the Inn on Fifth in 2022 for $156 million, the McCabe family needed a new space for their corporate offices. They found a remaining chunk of land owned by the Naples Airport Authority, where there was enough space to build a 5,500-square-foot, two-story office, as well as a 14,000-square-foot hangar, where the family parks their Dassault Falcon 900 EX.

While Joseph concedes that planes are depreciating assets (the money, he says, is in the parts), he regards them as important business tools. “The average national [charter] flight is one hour and 20 minutes with 2.5 people aboard,” he says. “At a rate of maybe $8,000 to $9,000 per hour, it’s an expensive tool. It’s a time versus money argument.”

Flying private has its perks. As Joseph cites, “you avoid the hassle of check-in, immigration, and security lines.” Flight plans can be filed quickly (an international flight requires only 24 hours). Plus, many jets function as a meeting space and can be specifically tailored to the occupants’ desires. “And Naples now has a customs facility,” Joseph adds. 

Rendering of The Carnelian, a new hotel and entertainment destination planned for North Naples by the Gulf Coast Commercial Corporation. Rendering courtesy of Gulfcoast Commercial Corporation
Rendering of The Carnelian, a new hotel and entertainment destination planned for North Naples by the Gulf Coast Commercial Corporation. Rendering courtesy of Gulfcoast Commercial Corporation

Initially, the Naples Airport began operating in 1943 as a military field. The Florida legislature created the City of Naples Airport Authority in 1969 as an independent government unit charged with the operation, development, and improvement of the Naples Airport. Keeping the airstrip operational allowed small niche carriers and commuter airlines to transport vacationers to the area. It also meant private planes (those under 75,000 pounds) could land in the heart of Collier County.

Naples became an accessible and attractive option as a vacation destination—especially for those who fly private. At present, the Naples Airport reports that approximately 200,000 passengers arrive or depart in a calendar year. Passenger surveys reveal that more than 80 percent of APF customers live in Collier County.

“Because of the location of APF, most people are within 10 to 15 minutes of their home when they land,” notes Joseph. In fact, he believes “there is no other town in North America that is as accessible from the private airport.” He concludes, “I don’t think Naples would be what it is today without the private airport.”

As business tools, planes can be specifically tailored to occupants’ wishes and often function as meeting spaces. Photo by Nick Shirghio
As business tools, planes can be specifically tailored to occupants’ wishes and often function as meeting spaces. Photo by Nick Shirghio

Looking Up

From his unique vantage point at the Naples Airport, Joseph confirms the luxury demographic is thriving in this community. For his family of longtime hospitality professionals, this knowledge helped solidify plans for what has become their latest project.

Through Gulf Coast Commercial Corporation, Joseph, his father, and his brother (Philip McCabe Jr., who founded The Vine Room, an upscale speakeasy on Fifth Avenue South in Naples) are currently developing The Carnelian hotel on land previously occupied by Beacon Bowl, located off US 41 (across from Waterside Shops).

A self-described avionics nerd, Joseph says flying private definitely has its perks. Photo by Nick Shirghio
A self-described avionics nerd, Joseph says flying private definitely has its perks. Photo by Nick Shirghio

Plans for the luxury landmark include 70 suites, two rooftop pools, a 20,000-square-foot wellness center, 20,000 square feet of dining space, and Sterling’s, a private club that will include a speakeasy called Jet Lag—an ode to Joseph’s business. The hotel and entertainment destination will “truly be a five-star property,” says Joseph.

“Seeing the air traffic gave us the confidence to develop a new property on a grand scale,” confirms Joseph, who will continue to help individuals reach exclusive destinations in high style and record time. 

Shot on location at the offices of Naples Jet Sales and Gulf Coast Commercial Corporation, Naples

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