"He's had a few little adventures of his own, he's got left behind a couple of times," Mr Diamond said.
Mr Diamond has been supporting himself on savings and the generosity of others and occasionally takes on work in exchange for his keep.
He recently did six hours of work on Glenburn Station on Wairarapa's east coast for two nights' accommodation.
And although he is not doing the walk for charity, many people have sponsored Mr Diamond such as Castlepoint Holiday Park, who put him up for three nights for free.
"The best thing of the lot is the kindness of strangers, people really helping me out, they give me a bed for the night, sometimes they might invite me in for meals and give me a cup of tea.
"I haven't got a support crew but by the time I get to the top I will have had 1000 supporters."
He said walking New Zealand's coastline is something he has always wanted to do.
"It's something I thought about doing 25 years ago but had too many commitments and then because of a marriage breakup I suddenly had no commitments."
Mr Diamond has avoided roads and has stuck to the east coast, preferring beaches where he can.
"Sometimes when I can't get to a beach I'll walk up a track and sometimes roads but I prefer to stay away from the roads."
It has taken him over a year to reach Wairarapa's coast, and on Monday, he was camping out at Castlepoint Holiday Park.
He is taking his time on his arduous journey to enjoy his surroundings and to recuperate and relax.
Yesterday, Mr Diamond headed north again and was hoping to make it to Owahanga.
Once he finishes his walk, he will be settling down with a new girlfriend he keeps in touch with via text message.
"It will just be a great sense of satisfaction when I get to the other side."
Mr Diamond is writing a blog and he has invited people to share the journey with him. "Hopefully some people will want to walk with me."
You can follow Mr Diamond's blog at wherespoppy.blogspot.com