The first to admit he's a stranger to the bicycle, Waugh, now 50, took up the recreation just four months ago.
It's fair to say, he's officially a MAMIL (middle aged male in lycra.)
"Yes I've been wearing the lycra but I can't say I'm that comfortable in it.
It's a bit of a different look, but I'm reasonably relaxed with it now, " Waugh said.
When it came to dominating the world's biggest arenas, few were better than Waugh.
"Children suffering from rare diseases are the orphans of the health system".
His tally of 32 centuries in an international career spanning 20 years was capped when named Australian of the Year in 2004.
He was revered when wearing the baggy green cap, but as a cycling novice he remains apprehensive.
"I still don't whether I can do it - that's part of the attraction.
"I'm testing myself to the max.
"I'm hoping I can rely on that reservoir of memories to get me through this."
Waugh will be joined by 60 riders when he leaves Sydney's outskirts on Sunday morning.
The ride will stop at various places along the way, including the Hunter Valley, Armidale and Grafton before coming to a grinding halt at Byron Bay on the NSW north coast on Saturday week.
He says children suffering from rare children diseases is a big issue.
"Children suffering from rare diseases are the orphans of the health system.
"We want to stand behind them and let them know they have a voice, they're going to heard and we're there to support them."
Waugh has been in deep training in his quest to cover the long distances on the road.
But not everything has gone to plan.
Preparation came at a price after falling off his brand new machine in his first attempt.
"I put my left foot in [the pedals], I was moving on an uphill slope," Waugh said.
"I missed my right foot, fell over and tried to rescue it - instead did a 16cm tear on my groin."
"It was the worst injury - the worst injury ever!" he added.
Waugh says he's a cycling lover and has a new appreciation for the popular activity.
He's a convert having only competed in sports involving a ball.
A one-time regular on the golf course, he hasn't picked up a club for nine months.
He chooses to ride by himself for now but he's the latest high-profile former athlete who has taken to the cycling culture which has gripped many Australians.
He's a regular viewer of SBS' international cycling coverage and is up late in July watching the Tour de France.
And while his days as a champion cricketer are well behind, he wants to make the biggest difference of all - on two wheels.
