"It was just something that cropped up."
His son, Andrew Judson, said he organised the skydive with an initial "apprehension."
"I said to him that I would pay for it but that he had to get checked out by the doctor first. He went straight in and got his clearance," said Andrew.
Mr Judson said the feeling of free falling was his favourite part of the skydive.
"You don't feel as if you're moving at all, It feels as if you are floating," said Mr Judson.
He said when the parachute was pulled, it gave him a chance to take in the "brilliant" view of "all the ocean and the mountains" below him.
About 20 family members waited to congratulate Mr Judson at the base of Skydiving Kiwis as he came down to land.
"They were all surprised I actually did it," said Mr Judson.
One of the family members was his 94-year-old sister who flew down from Auckland for the first time since before the Christchurch earthquakes to watch her brother take the plunge.
"It was really great to have her down here for it," said Mr Judson.
Mr Judson said he had "never met a friendlier bunch of people" than the team at Skydiving Kiwis.
His instructor, Dakota Keen, said the entire skydive "flowed really nicely."
"I was a bit nervous at the start because he has had a couple of health issues but we saw through them and he did everything he was asked to do."
Mr Judson was the oldest person Mr Keen had ever been in a tandem with.
"It was amazing, it was a great honour for me," he said.
As far as the next item on Mr Judson's bucket list goes, he said he is just focussed on reaching his next birthday.
But he does have one ultimate goal – which is to do another skydive when he gets to his 100th birthday.
This story was first published in the Otago Daily Times.