Ms Westoby has already completed two free falls - one in Wanaka 10 years ago, and four years ago above Franz Josef Glacier - but twice she has tried, unsuccessfully, to make the jump in the Queenstown area over the past two years.
"Both times the weather was rotten, and of course you can't do it," Ms Westoby said.
"I might stay a night or two and hope and pray for a bit of sunshine."
Like the tattoo, she hopes to use the skydive to publicise the aims of the Exit International - an organisation advocating free choice for people wanting to end their lives and promoting acceptance of assisted suicide - and for which she is Dunedin convener.
She said although she would never bungy jump, the adrenaline rush from skydiving was wonderful and it would be "absolutely marvellous" if she died doing it.
"I mean, I wouldn't like it to be an accident so that the man on whose knee I'm sitting, he himself would be hurt. But there was a man who jumped, he was 81 and had a heart attack while coming down. He died, and when he hit the ground he had a great big smile on his face," Ms Westoby said.
