What It’s Really Like Piloting Private Jets For The Rich And Famous

Flying privately owned aircraft gives pilots a unique lifestyle within the spectrum of aviation jobs. The set of challenges they face can be very different from those of flying airliners. Among the greatest challenges is passenger behavior. In a short period of time, pilots are all but guaranteed to experience some of the wildest interactions and witness some of the craziest behavior of their lives. Unlike on an airliner, these are not passengers boarding a flying bus usually for the lowest fare possible. They are by their very nature highly demanding VIPs that come with a whole different set of unique pitfalls and maddening roadblocks.

Within the realm of flying private there is flying for charter, sanctioned under 14 CFR FAR Part 135, and flying for an aircraft owner directly, which falls under 14 CFR FAR Part 91. All general aviation that is not operated for hire is conducted within the rules of Part 91. Whether the aircraft you’re flying is a Piper Cub or a 747-8i, if the flight is not being conducted for hire or compensation, it’s a Part 91 flight. Charter flights are private flights where an individual or organization is paying to be flown in an aircraft they don’t own. 

A Gulfstream business jet takes the sky from Aspen’s high-altitude airport. , AP

My experience is exclusively Part 91, in a variety of aircraft that has included small piston aircraft, turboprops, and jets. The size of most privately owned aircraft means there is no flight attendant. The pilot or pilots are often the sole steward and liaison for their passengers’ and owner’s experience. Most turboprops and light jets are certified for operations with a single, appropriately rated pilot, leaving that one pilot responsible for everything.

Everything means everything. Safety of flight, flight planning and flight plan filing, passenger comfort, and often travel accommodations. Every pilot in Part 91 and 135 aviation sets out to provide the best travel experience possible. If they can’t provide that, the motivation to fly private goes away. 

Do you need a picture for Instagram to brag that you flew on a private jet? Pilots are happy to help. Special meal or drink requests? Sure. $100 bottles of whiskey pale in comparison to the multi-thousand dollar fuel bill for a short trip to a sports game for the day. 

Passenger reactions range from humble and thankful to taking advantage of the situation and behaving in ways that would get them thrown off an airline flight and potentially even arrested. 

Photo by ViewApart

I’ve conducted flights on which passengers brought their own alcohol and became so inebriated they were screaming in the center aisle and ripping their clothes off—one in particular on the runway after landing in Las Vegas. 

Most airline pilots can’t say they have had to corral and manage a drunken passenger after shutdown to prevent them from running down the flightline while waiting for ground transportation. Less than two hours later I was notified that this passenger had another outburst. As a result, they had been detained, threatened with charges, and banned from the casino at which his group was staying. Being sober, my help was sought in mitigating the fallout and begging the casino to reverse the ban to save the trip as planned.

I was unsuccessful.

Most pilots who fly charter and Part 91 have celebrity stories. In almost all cases it is important for the industry to respect privacy. If a company or pilots were to provide tabloid media with pictures or information about the habits of celebrities it would be bad for business. Still, among friends and associates, stories inevitably get out. The proliferation of online industry forums doesn’t help, but most pilots remain tight-lipped in the public domain about their passengers. 


On private forums many years after the fact, flight crew members attested to their experiences as explosive tabloid stories broke regarding Britney Spears’ mental breakdown. They were called to the jet earlier than expected for an expedited departure and were shocked to see her arrive with a shaved head. Her entourage was eager to get her out of the public eye.

All is not as it seems. Before negative news broke about Bill Cosby, a close friend related his experience having flown him. At the time Mr. Cosby’s public image was still that of a gentleman—”America’s dad.” My friend was taken aback by his aggressive demeanor and generally poor treatment of the entire flight crew. 

On a charter trip out of Van Nuys, a well-known actress calmly sat for an entire flight while her children scratched, cut, and drew on the entire interior of a large private jet. The cost to refurbish the interior of a cabin aircraft ranges greatly in price. In this case, the damages were over $250,000. She was sent a bill by the operator, but she refused to pay it. Litigation was determined to have the potential to have a negative impact on that charter company’s reputation for celebrity service in the Los Angeles area. The matter was not pursued and the charter company was never compensated. 

The CEO of a major restaurant company chartered a private jet for the extremely short flight from Aspen to Denver. His family smeared mud and pizza sauce everywhere. No, the pizza wasn’t from his chain and the cleaning bill was $2,100 dollars.  

Lade Gaga exits a Gulfstream—while celebrity private air travel gets the most attention, thousands of wealthy families and corporations own private aircraft or leverage private air travel. Many of these people are used to getting what they want when they want it. As such, it can be challenging to balance demands versus reality and flight safety while also keeping the guest satisfied. , AP

With no gate agent to cover for them, pilots of private aircraft also bear the burden of relating news of maintenance and weather delays to passengers. Experienced passengers recognize their flight would most often be canceled had they been traveling by airline. Flying private affords the luxury of adjusting departure and arrival times within the passengers’ schedule to mitigate weather that would otherwise prohibit flight. On rare occasions, the passengers, accustomed to getting anything and everything they want at a moment’s notice, rage at their pilots about being inconvenienced.

I’ve flown through weather conditions on descent that made passengers queasy. Getting assigned holding during inclement weather, which is flying a racetrack pattern in a specific place for the purpose of maintaining arrival sequence and separation, can usually make at least one passenger feel less than optimal. For passengers, holding and significant turbulence with no visual horizon reference is a combination that can take down the best of them.

On one occasion flying into Hillsboro in Oregon, this exact scenario made every passenger miserable. My flight plan was carefully timed to arrive after a line of storms and before the next one was due to arrive. Pilots will tell you a thunderstorm can contain almost every significant meteorological weather hazard. When the passengers were ready to depart, a line of thunderstorms was directly over the top of the airport. The lead passenger, still sick from our arrival, was livid that I delayed our departure, even after it was explained that what we experienced on the way in pales in comparison to what we would experience with an immediate departure. Every pilot in command is the sole decision-maker and bears 100 percent of the responsibility for the safety of flight. The pilot of a privately operated flight is the focal point of the owner’s and passenger’s anger for being inconvenienced. 

The convenience of private air travel is like nothing else, but it comes at a high cost and those paying the bill expect far more than a seat on an airplane., Hugo3055 via Wikicommons

Just as a decision to fly an aircraft requires research and forethought that is put to the test when you go fly, a decision to delay departure for maintenance or weather is frequently put to the test by your passengers. When your passengers are unhappy, and one of them pays your salary, it feels like your job is on the line, and it very well could be. They don’t teach you in flight school how to navigate situations like this. You learn from both experience and other pilots to stay calm and professional while being ready to explain and back up your decision. It’s not easy to keep your cool if someone is yelling at you. You have to remind yourself how clueless they are, and that you’re their liaison to safe flight. 

The fact of the matter is that a pilot might be one of the only people in a jet owner’s life to tell them no. The wealthiest among us are used to getting their way. I’ve seen extreme tantrums and even threats. If a passenger applies extreme pressure to a pilot in an effort to assert their will, and the flight results in a weather-related accident or crash, it’s never the passenger’s fault. It’s the pilot’s fault.   

It’s certainly isn’t all bad, but every trip is unique and every pilot in private aviation has a wild story or two. Most have many. For instance, private aviation may be the only sector where the passengers are in a position to request a low altitude flight. Reasons include seeing their property from the air or impressing their friends with jet noise, which can be underwhelming in quiet late-model jets.

A Cessna Citation CJ4 business jet., Cessna Citation/Textron

Within the confines of Federal Aviation Regulations, which generally prohibit flight under 1,000 feet of the surface and faster than 250 knots, you can still have a great time. Parks and wildlife preserves are off-limits too. Passengers accustomed to flight at 45,000 feet, and higher in some cases, are thrilled by a ten-mile run over their ranch at 1,500 feet and 200 knots. 

The future of airline flying as we knew it is uncertain, but in late 2020, the use of private aircraft is skyrocketing. Business for charter operations is booming. I have personally always found private aviation to be the most intriguing kind of flying, and my experiences participating in it were never dull. 

The author is a United States Air Force veteran and 5,000 hour Airline Transport Pilot and Commercial Helicopter Pilot, type rated in private jets and with over a decade’s experience managing and flying private aircraft. He has a wide breadth of experience in aviation, having flown people from all backgrounds into and out of everything from small mountain airstrips to large international airports.

Contact the editor: Tyler@thedrive.com