But the bizarre journey of Marcus Schrenker was over. His next stop would be a jail cell. He was hit with two federal charges: filing a false distress call and intentionally destroying an airplane.
Schrenker pleaded guilty and now is serving 50 months in prison.
While he admitted in court documents that he deliberately tried to crash his plane in the gulf, he told "20/20" several different versions of the story, saying his bipolar disorder and painkillers left him in a confused fog.
The closest he came to admitting the truth was this: "It absolutely points to a premeditated desire to run, fake the death, crash the airplane, because of the motorcycle, because of the forward planning," he said. "It's hard for me to grasp."
Aside from the disaster in his personal life, Schrenker's business dealings were about to land him in hot water. The state of Indiana was about to charge Schrenker with fraud. On this matter, he was mute.
"20/20" asked him whether he had run his companies above board, or whether there had been anything that could be perceived as fraudulent.
"I'm sorry, I can't answer that," Schrenker said. He said he was innocent of the Indiana charges.
As Schrenker sits in jail, his wife, Michelle -- the divorce isn't final -- and their three children have moved out of the family's mansion. They are struggling to get by.
It's a turnabout that seems to stir the only genuine reaction in Marcus Schrenker.
"My oldest son, Tyler, has been put through hell because of what I did," Schrenker said. "And he is such a good kid. My daughter, Alyssa, she's so beautiful and wonderful. And my younger son, Jayden. I love all of them so much. I am so sorry for the pain I have caused them."