Family members describe him as a "thrill-seeker", and Peter Pfister said celebrating his 90th birthday by jumping out of a plane was an exceptional experience.
"I've done everything except Mount Everest," he said.
"I couldn't believe I'd done it. I wouldn't say it would be suitable for everyone... But once I commit to something I go through with it."
Mr Pfister, a father of four, grandfather of six and great-grandfather of one, is a resident of Illawarra Diggers Aged and Community Care at Corrimal.
He turned 90 last Friday, and on Sunday celebrated by skydiving for the first time.
Also taking part in the tandem jumps on Sunday morning were Mr Pfister's sons Grahame and Neil, as well as son-in-law Tony Parry.
"I didn't think he'd be fit enough, but they reckon he is, so well done to him," Grahame said.
The jump was run by Skydive Sydney-Wollongong, with the participants landing near Fairy Meadow surf club.
Minutes after landing, Mr Pfister laughed and told the Mercury he felt "100 per cent, now that I've stopped".
"I've been up that high many times, but never in one of these things," he said.
"When they said, 'you're going out there', and we jumped out the door, I looked down and thought, 'oh my God, what am I doing?'
"Going 250km/hr is a little bit hard, isn't it?
"All I'm looking for now is a pub to have a beer."
Family members attended the landing, and had a birthday lunch afterwards.
One of Mr Pfister's daughters, Maria Parry, was present to watch the landing.
"He was the thrill-seeker out of Mum and Dad," Mrs Parry said. "He has a real appetite for life. He's trekked in the Himalayas, and done a lot of world trips."
His other daughter, London-based Janice, a former champion parachutist, was unable to be there.
At age 21, Janice attempted a jump at a championships in Victoria, but the wind changed, and she landed on 22,000 volt power lines.
She lost her arm and suffered severe burns to her hip.
After five months in intensive care, she eventually returned to parachuting.
Unfortunately, the wind changed again, she hit a tree and was knocked unconscious. She then retired from parachuting.
Due to this history and for fear she would convince him not to do it, Mr Pfister had attempted to keep his skydiving plans secret from Janice until he had successfully completed the jump.
However, she found out two weeks ago and was the first person to speak to him after landing.
"She was very happy with it, even though she had that terrible accident," Mr Pfister said. "She said, 'Dad, I'm proud of you for doing it'."
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