Geoff Dean, who was also celebrating his 74th birthday, braved the skydiving challenge alongside his three children and two grandchildren.
His ex-wife and mother to his children, Pauline Stringer, sadly passed away in 2012 after an 18 month battle with Progressive Supranuclear Palsy.
The Parkinson's-like neurological condition is caused by the premature loss of nerve cells in certain parts of the brain.
Geoff. from Wilberfoss, East Yorks., said: "I thought it would be a great achievement if we could get three generations of our family doing the skydive together."
The family are hoping to raise around £7,000.
Joining Geoff will be his children Graham Dean, 52, Joanne Ferguson,49, and Claire Castle, 42, and grandchildren Aiden Dean, 24, and Dana Ferguson, 20, will all be joining him in the challenge.
Daughter Joanne said: "We were trying to raise as much money as possible as my mum died back in 2012 from a very rare brain illness called Progressive Supranuclear Palsy (PSP) - she was sadly only 68.
"She started doing odd things that we could not put our fingers on a couple of years before that - she had "stumbles" both forwards and backwards, then she would write something and her writing was really odd and she could not spell things anymore.
"We assumed it was linked with her diabetes, but then she started slurring words and leaning to one side when she was sat in a chair - eventually after having numerous test and blood clots etc and other brain illnesses were ruled out, we finally got the diagnosis.
"By this time, she had deteriorated rapidly and had to go in a nursing home for palliative care in Leeds - this was also a challenge as there are so little people that know about the illness.
"Sadly, mum passed away in Oct 12 only 18 months after diagnosis."