The incident happened in Northport Harbor at the Centerport Yacht Club around 3 p.m., while the victim was taking a sailing lesson with two other students, all wearing life vests.
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"We were just pulling in, actually when they brought him to the dock. It was terrible," said Scott Koolik, a boater.
Koolik said the scene was shocking.
The bleeding child was rushed to the dock. There were desperate attempts to save him as distraught parents raced to the harbor to comfort their children.
"We saw all those kids, we didn't know what was going on yet, the little kids were just taking their lessons and stuff, and then we saw the police and the rush to the dock. We pulled in and we just couldn't believe what we'd seen. It's a shame," Koolik said.
Authorities say the boy was struck by the propeller on the outboard engine of an inflatable boat, known as a Zodiac.
It happened after he and two other junior sailors were practicing a capsizing drill in a small sailboat called a Feva.
The boy was pulled from the water and into the Zodiac by his 18-year-old instructor, but investigators say he apparently lost his balance.
"When that Zodiac went to accelerate to bring the boy to safety, that child again fell off the Zodiac and became entangled in the propeller," said Det. Sgt. James Scimone, Suffolk County Police Department.
By some accounts, the boy's life preserver may have been caught up in the propeller. The child suffered massive injuries to his chest.
The instructor performed CPR until EMS arrived, and the child was rushed to Huntington Hospital, where he was pronounced dead.
There was no immediate comment from the Centerport Yacht Club, which authorities say runs the sailing program.
The instructor was not identified Monday night, but was said to be inconsolable.
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"Imagine the parents, it's just awful," Koolik said. "When you have children, you're doing a summer activity, it's the last thing you'd expect. I'm sure it's no one's fault, accidents happen. But it's awful. There's definitely a dark cloud over everything."