But four days later, on June 19, a parasailing experience changed all that. Henry Owens slipped as he was moving from the parasailing boat onto the banana boat that was to take them back to shore.
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"I remember going underneath. The propellers were there. I was trying to work my way up and my legs got caught in the propellers," Owens said.
What happened next was both gruesome and traumatizing. Initially relieved to see him surface, it was not long before Owens' wife, Melloney and their two boys realized the full extent of his injuries.
"As we pulled him across the edge of the banana boat his left leg fell off from the knee down," she said. "My son is seeing this. I'm seeing this. And we're still pulling him, and as we pull him completely in the boat the right leg is completely mangled. The foot is just dangling and the leg is hanging on by a couple of strands."
Owens was placed in a medically-induced coma for two days. Both his legs were amputated above the knee.
Owens was transferred to Lutheran General in Park Ridge so he can rehabilitate closer to his Carpentersville home, which will need to be remodeled to suit his new needs. At some point he will be fitted with prosthetics.
Owens' goal is to eventually be able to play basketball and football with his sons again. For now, however, his focus is on little things, like learning to go to the bathroom on his own and getting answers from Ocean Watersports, the company that ran his parasailing trip.
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"If the boat when it was sitting next to the banana boat, had just turned off its motor and had it at idle, this wouldn't have happened at all. I would have my legs right now," he said.
In a statement to ABC 7 Eyewitness News Ocean Watersports owner Jim Alford said: "Ocean Watersports is deeply saddened as a result of the injury to our customer. As active members of the Watersports Industry Association, we pride ourselves in our safety practices and safety record over the last 38 years. Our licensed captain and crew acted immediately to rescue our customer after the incident. We are keeping our customer and his family in our thoughts and prayers and wish him well."
The U.S. Coast Guard in South Carolina is still investigating the circumstances, in what is a largely unregulated industry.
A spokesperson telling us that the company involved does not require inspection because their boats carry fewer than six people.
The family has set up a GoFundMe page for donations to help them with expenses associated with the double amputation.