The plane took a nose-dive and the skydiver was thrown to the ground at the airport in Polk County.
Neither the pilot nor the 49-year-old skydiver were seriously injured when they fell about 75 feet, according to the Polk County Sheriff's Office.
Sharon Trembley, 87, was doing what are called "touch and goes" with the Cessna, a maneuver in which the plane touches the ground and ascends again.
On his third time up, one wing became tangled in the strings of the parachute that held John Frost, officials said.
Both men were taken to a hospital. Frost was treated and released and Trembley was being held for observation, the report said.
Officials said the National Transportation Safety Board and the Federal Aviation Administration were notified and responded to the scene.
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