Typically preparations for a trip start in the flight planning room, where the pilot calls the flight service station and gets the latest weather information. "Then by calling the flight service, they would take my registration number and have a record of the fact that I familiarized myself with the weather along the route," Grady told Diaz-Balart.
The next step before takeoff is a visual inspection of the plane, which takes anywhere from 15 minutes to a half hour. From checking the propeller to inspecting for leaks of fluids on the ground, it's all quite logical - and vitally important.
"It isn't like a car," said Grady. "You know if you jump in your car and you get out the driveway and you forget something, you can stop the car and fix it. But with the airplane, you want to make sure everything is right.
Inside, the plane has room in the cabin for storage, four passengers in the rear, and the pilot and another passenger in front. There are checklists for takeoff, a climb, cruising, descent, prelanding and landing.
"The checklist is a reminder so that we do everything in the same order and we're less apt to forget things that way," said Grady.
When it comes to a pilot flying under visual rules, the most important part of the checklist would be tuning the plane's communication system.
"That automatically puts a signature on the radar," Grady said.
Grady, who was flying the night Kennedy was, called the conditions on his later flight with Diaz-Balart virtually the same. Once airborne, the bright lights of the Meadowlands Race Track lit up the surrounding sky. But in the distance, the Empire State Building was shrouded in haze.
As the flight progressed up the coast, away from the bright lights of New York and its suburbs, the lights were harder to pick up. The haze seemed stronger, until out over the water, there was no light at all. This is where a relatively new pilot, flying on sight alone, could encounter serious problems.
"To the untrained eye like mine," reported Diaz-Balart, "it seems like it's very difficult to know where the heck you are because it's all pitch black out here."
"That's, I think, the reason that they invented the instruments," said Grady. "The requirement in order to fly visually is that I need to be able to see three miles around the airplane.
"So if I happen to fly over a woods or a body of water or something where there are no lights within three or four miles, it becomes physically impossible for the human eye to differentiate between the sky and the ground," he observed.
"I could look out - I culd see some boats on the water - and they might look like stars. It's very easy to become disoriented. You could inadvertently go all the way upside down," he added.
When heavy haze or cloud cover takes away all the references, a pilot can become disoriented, assuming the plane is flying parallel to the ground, when, in fact, it could be flying sideways. What is thought to a left turn might actually be a climb, and what is believed to be a right turn, actually a dive.
Instruments become a potential lifesaver. For a pilot in trouble, they can provide a relationship to the horizon, literally keeping the plane flying straight. That's what Grady relied on to fly Diaz-Balart to the Martha's Vineyard airport.
"Nighttime over the water, there is nothing lit on the water so you're over a big, black spot," New Jersey flight instructor Tim Simard told CBS News Correspondent Maggie Cooper.
Every pilot learns the basics about cockpit instruments, but an instrument rating takes far more training, which Kennedy didn't have. "An instrument pilot who can't see the ground or the horizon is going to keep his wings [level] using that instrument," said Simard.
Kennedy was flying by visual flight rules, or VFR, that hazy Friday night. And Simard said a pilot without an instrument rating in that situation "shouldn't be where he is."
That same night corporate pilot Alan Leiwant flew to East Hampton, N.Y., from the New Jersey airport. "Everything was black and murky," Leiwant said. "I wouldn't want to be a VFR-only pilot flying in those circumstances."
WCBS-AM Radio Anchor Ben Farnsworth, a pilot who had made the trip many times by day, admitted that on a similar night, on a similar flight, "We blew right past Martha's Vineyard."
"Once you get past the west coast of Rhode Island,...there's just water below you; it's a black hole, he added. "And there aren't a lot of lights on Martha's Vineyard either.
"Under certain conditions, for an inexperienced pilot, with haze, it can be a difficult and challenging event," he said.