On July 16, 1999, John F. Kennedy Jr. was confident in his flying abilities as he prepared for a short trip to Martha's Vineyard. According to the National Transportation Safety Board's report, taken in July 2000, Kennedy told his flight instructor, Bob Marina, that he didn't need him on the day of the flight.

Marina recalled offering his services, but Kennedy replied that he wanted to do it alone. That decision ultimately ended in tragedy, as Kennedy, his wife Carolyn Bessette, and her sister Lauren Bessette all died in the plane crash.

The plan was for Kennedy to fly his Piper Saratoga from Essex County Airport in New Jersey to Martha's Vineyard in Massachusetts. He would drop off Lauren before he and Carolyn continued northeast to Hyannis Port for his cousin Rory Kennedy's wedding.

At the time, Kennedy was in the process of obtaining his instrument rating, an aviation certification that allows pilots to fly by relying solely on cockpit instruments rather than visual reference. However, his flight instructor told NTSB investigators that Kennedy may have had issues while flying given the poor and hazy weather conditions on the night of the flight.
Marina said he was not comfortable with Kennedy flying at night in weather conditions similar to those during the accident, and along a similar route. He added that Kennedy was not ready for an instrument evaluation at the time of his death and needed further training.
The NTSB's report states that the plane took off around 8:39 p.m. A little over one hour into the flight, the plane took a left turn and began a descent, crashing into the Atlantic Ocean during the hours of darkness. All three passengers on board were killed.
The aircraft wreckage was recovered four days later, about a quarter mile north of its last reported radar position. The crash is expected to be included in the March 26 finale of *Love Story: John F. Kennedy Jr. and Carolyn Bessette*, a biographical account of the couple's lives starring Paul Anthony Kelly and Sarah Pidgeon, airing now on FX and Hulu.