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Karlyn Connolly (41) arrived in Balclutha yesterday on his way to the Catlins and is due to reach the end of the first leg when he arrives in Bluff tomorrow.
Mr Connolly left his job in Hamilton and sold everything he owned before he set out from Picton on February 1, for a 96-day tour of the country.
He is cyling around the South Island, as close to the coastline as he can, before crossing the Cook Strait and doing the same in the North Island. He plans to end his tour in Wellington on May 7.
Mr Connolly is travelling without a support crew, carrying out his own bike repairs or with the help of local mechanics, and camping ''wherever I can'', including on the side of the road.
This is the second time Mr Connolly has embarked on the journey. He completed his first ''Cycle4Life'' tour in 2010.
He weighed 142kg when he started his first trip and lost about 20kg riding his home-built mountain bike on the 6237km journey, towing a trailer loaded with gear.
He said he was fitter and better-prepared this time, learning from the mistakes of the first trip.
''I had one and a-half months' worth of food, magazines to read when I was bored, changes of clothes, bike parts - all sorts [of rubbish], really. I only had two 500ml bottles of water. I had no idea what I was doing.''
This time around, he knows what he is in for.
''I know what I'm doing now. I'm resilient, flexible and stubborn. This time it's not about me and the ride, it's about raising awareness for charities. I want people to think about charities and what they do, and think 'How can I help them?' ''
If anyone wants to give money to a charity, Mr Connolly asked that they give directly to the charity of their choice. However, if people want to sponsor ''Cycle4Life 2'' they can give through his website www.customvision.co.nz.
Mr Connolly said he had met a woman in Blenheim who said she was going to search for her adult son, while a Picton man planned to assist his local hospice group after they helped his family.
''At the end of the day, if people like these two do what they said they would do, then I'm making a difference.''