Recollections of the rigours that accompanied five-day Test matches will pale alongside the challenge that faces former Australia skipper Steve Waugh and his crew as they confront the daunting realities of Victoria's high country in the latest iteration of his 'Captain's Ride'.

Waugh is back on his bike for what he believes will be the most gruelling campaign of the six-day cycling and mentoring event that he pioneered four years ago, and which he hopes will raise more than $1 million to help children with rare diseases through the Steve Waugh Foundation.

This year's event will take riders into terrain that folklore more readily equates with high plains horsemen astride wild brumbies, from sub-alpine townships such as Bright and Beechworth under the shadows of Mounts Hotham, Beauty and Buffalo.

The circuit covers around 800 kilometres with total distance climbed aggregating almost 10km, which – as Waugh ruefully notes – is equivalent to the altitude at which jumbo jets travel.

For the 53-year-old, who was more comfortable compiling his runs in 22-yard dashes across 168 Tests and 325 one-day internationals, the transition to road cyclist hasn't come without a measure of pain and a lot of learning.

"It sounded like a good idea at the time," Waugh reflected with a wry smile of his decision to incorporate the annual cycling event as a cornerstone of the Foundation's fundraising activities.

"The first year we put the event on, I thought 'I've got to start riding a bike' because I hadn't ridden a bike (that distance) and physically I was a mess after the first one, so I've trained for each ensuing ride.

"It's physically and mentally a real challenge, but it's meant to emulate the spirit of the kids that we support.

"It's what they show every day; they show determination and courage.

"They get on with it, they don't complain and they work together.

"So that's the idea of the ride.

"We do it for tough for six days; the kids we're supporting do it tough each and every day of their life."

Such are the physical demands placed on those who sign up for the ride that the huge logistical effort overseen by Waugh's wife, Lynette (who volunteers around 50 hours a week), includes masseurs, doctors, physiotherapists, documentary film makers and safety personnel.

It means the total peloton of riders and support crew for the six days now numbers more than 100.

However, the physical demands are mitigated by the mentoring component of the event that includes nightly presentations on leadership from inspirational speakers including (on this year's ride) Olympic 400m gold medallist Cathy Freeman, and Waugh's ex-Test teammate Merv Hughes.

Among those speakers who will also jump aboard a bike for some, or all of the six-day journey are cycling champion Anna Meares, legendary British decathlete Daley Thompson, Olympic pole vaulter Steve Hooker, former Liverpool footballer Craig Johnston and adventurer and author, Tim Cope.

"I wanted to create events for the Foundation that would be life experiences – rather than having fundraising dinners I wanted people to have an experience," Waugh told cricket.com.au.

"It's a pretty incredible event where people get to ride alongside these icons of sport to learn about sport and business.

"At the same time, they learn about sport and business, and raise awareness for the Foundation and raise money, and they do something they never thought was possible.

"So it's a life-changing week for a lot of people.

"We always go the hard way, and that's part of it.

"People complain every year and say 'can you pick an easier route, can you make it more comfortable' but no, it's meant to be tough.

"It's meant to challenge you in every way.

"If people get through that they feel really satisfied and that's a big part of why people come back because it's not easy, and it's not meant to be easy.

"This year it's the Victorian highlands and it's the hardest destination, I guess, that we've chosen so far.

"Each ride we look to raise over a million dollars, and that looks after our grant recipient programs for a year.

"We spend over a million dollars handing out individual grants to the kids, and that really is a core essence of the Foundation.

"Every dollar raised goes directly to supporting the kids."