Rawlinson and stage one crew mate Charlie Smith, a 26-year-old investment banker from the UK, today pushed off from Raffles Marina in their state-of-the-art ocean rowing boat Simpson's Donkey bound for Darwin.
The 4500km route through the Indonesian Archipelago has never before been attempted in a rowing boat or by human power.
The pair will row in 2-3 hour shifts, non-stop, 24-hours per day for days and weeks on end.
The rowing boat, built from a blend of carbon fibre and fibreglass, carries a water maker, solar panels for power to run GPS and communications systems. It has a small cabin for shelter and sleep, and in the event of rough weather and capsize, is designed to be self-righting.
From Darwin, 42-year-old Rawlinson will travel 4500km by bicycle across the Australian continent to arrive on the east coast of Australia, where he will then row almost 3000km across the Tasman Sea to New Plymouth.
Rawlinson, who regularly works as a keynote speaker for companies interested in tapping into his inspirational stories, said the expedition may have started today, but is over two years in the making.
"These journeys have significant risks and we put a massive effort into the planning and preparation phase to mitigate the significant risks involved in these journeys," Rawlinson said.
"The main reason I am undertaking this journey is for the adventure, to explore some diverse areas of mother nature and to push my limits."
Every step of the expedition will be documented, including the use of an advanced GPS tracking system allowing supporters to follow the progress in real-time, 24 hours a day.
"I hope to share this expedition with as many people as possible especially the younger generation including my own children, to inspire and send to them positive messages that we can achieve massive goals in sustainable ways without destroying the environment in the process," Rawlinson said.
Rawlinson is filming the expedition together with Singapore-based Kiwi film maker Alistair Harding who will be producing a series of short-films throughout the journey along with regular updates from the crew of their progress posted to their Facebook page.
Rawlinson hopes to reach New Plymouth in November or December this year, where he will cycle the remaining 40km to his home in Stratford.