Mr Buckingham (33), a sheep and beef farmer from Waimahaka, in Southland, is heading to Mystery Creek this week to compete in the ultimate challenge - the Fieldays' Rural Bachelor Best of the Best competition.
Eight previous Fieldays' Rural Bachelor of the Year winners have been invited to compete in a special edition to determine the supreme winner.
Most - including Mr Buckingham - have found love, so are not strictly bachelors, with only two contestants describing themselves as single.
Mr Buckingham, the only South Island winner, won the Gumboot in 2005 and was also the People's Choice winner.
The experience was "good value", and had placed him outside his comfort zone.
Now engaged to Karen Colhoun, his "perfect woman - smart, hot, has a great sense of humour, a great attitude and more", the prospect of a trip to the Cook Islands was in the back of his mind as he headed north.
"It wouldn't be bad to go up there and say, 'Hey honey, I've just got our honeymoon sorted out'," he said.
The winner will receive a trip for two to Rarotonga, a motorcycle, clothing and vouchers.
Mr Buckingham said he was "not going up there just to make up the numbers".
Challenges include fencing, horse handling, general knowledge, dog handling and excavating. His equine skills were "sweet as, no worries at all". He did, however, spend some time on the digger last week "just to freshen up".
A cooking module was also expected to be on the list of tasks. Describing himself as "pretty old-fashioned" in the cooking department, producing "good country tucker", he was slowly increasing his repertoire.
"I wouldn't say I'm a chef." One of the challenges that proved more difficult in 2005 was the pamper session. Having to get a woman out of the crowd and give her a hand massage was "probably not a southern man's real finer points", he said.
Asked whether he achieved celebrity status after his win, Mr Buckingham said it was easier to slip under the radar in the South.
Some of the North Island winners were more recognisable, with the image of one featuring on the side of a bus. Waimahaka did not even have a bus, he said.
He expected this year's competition to be more difficult and he hoped he had still "got it".
"Time will tell. The gumboot should belong in the South." The other contestants are Mat Sherriff (Te Awamutu), Christen Diamond (Waitomo), Paul Slater (previously from Te Pahu and now in Australia), Mark Woodcock (Dargaville), Charlie Taituha (Piopio), Mike Short (Sanson/Bulls) and Nick Torrens (Te Aroha).