By his own admission, he is not one to do things by halves, so the team or two-day individual sections were never considered as stepping stones to the main event.
After 15 years in banking in Auckland, Sydney and London, Wilson (39) decided to take a break and moved to a lifestyle block on the Taieri with wife Philippa and children Sophie (12), Jemma (9) and Finn (7).
He has done plenty of running and swimming, but the 67km kayak down the Waimakariri River in his first Coast to Coast presents a new challenge.
''What I thought was the easiest is proving the most challenging,'' Wilson said.
''You just can't sit back and go for a ride. My swimming ability has certainly come in handy.''
Wilson was a promising junior sprinter while a member of the Ariki Athletic Club, and played rugby and cricket for Bayfield High School's top teams.
Before leaving for his first stint with Deutsche Bank in Auckland, he played rugby for Pirates, Otago Colts and Otago B. He then played for North Harbour Marist, North Harbour B and the Harbour sevens team, before joining Manly after a transfer to Sydney.
Wilson pulled the pin on rugby 10 years ago, but continued to run a couple of times a week and have an occasional swim session and bike ride.
When he returned to Auckland in 2006, after three years in London, Wilson was drawn into triathlon and half ironman, in which he has proven to be very competitive.
Upon his return to Dunedin, he was enticed to crew for a former schoolmate, Glenn Sutton, in the Coast to Coast.
''I always knew this race existed, but never really gave it any thought,'' he said.
It has been a long journey over the past year as Wilson prepares for the 2014 ''great race''.
Apart from training with Sutton and soaking up his knowledge, Wilson is full of praise for Otago marathon and multisport identity Bill Godsall, who helped him gain his grade 2 kayaking certification for the race.
''Bill just gives so much back to sport and most of it's voluntary.''
Wilson said his main goal was simply to finish and to be able to reflect on his efforts afterwards with pride and satisfaction.
Sutton completed the longest day course last year in 15hr 53min 19sec. Wilson is not expecting to break the tape on Sumner Beach before his friend.
''Somewhere close behind would be nice.''
