"I really looked up to them and I used to follow them around the course so when they tacked, I tacked," says Gilmore who will line up in the five-day Napier Sailing Club-hosted regatta which will beckon 177 aspirants from throughout New Zealand as well as those from New Caledonia, Australia and Tahiti.
"I was never beating them because I was always following them," says the teenager of the Thursday night sailing and whole day Saturday club regatta along the Ahuriri waterfront.
But about four months later the then 12-year-old did the unthinkable - changed tack and took a different route to the fleet.
"I beat them all for the first time."
That wasn't just a snapshot of his inherent talent but also epitomised his willingness to step out of his comfort zone since a mate, Nick Mannering, coaxed him to continue what he had picked up from a school holiday programme that club member Marty Weeks had conducted.
The soccer player relished the challenges of sailing although the cold water proved to be a deterrent so not capsizing the vessel became an incentive.
"I wasn't afraid [about the cold] or anything but I would rather keep it [the boat] upright. It was quite a natural thing for me and I learned it real fast."
For the record Gilmore is ranked No9 equal among optimist sailors in the country.
Club stalwart Adrian Mannering had helped him immensely and his daughter, Nina, then 11, trained alongside him.
"Nina had started sailing three years before me so it was quite cool watching her," he says, recalling the frustrations of trying to bridge that gulf.
In hindsight, Gilmore sees the value in learning alongside others who were much better than him because it made him strive.
At the end of the first year, he attended a five-day coaching clinic at Eastern Beach in Auckland among 50 peers, including some of the top 10 in the country.
"I picked up little things that make you go that extra faster," he says, gaining invaluable insight on how much harder he had to toil to be considered an elite.
Late last year Gilmore finished seventh at the optimist nationals staged in Auckland, agonisingly missing the top-five cut to book a berth at the world championship.
He didn't despair. Another door opened - in Crotone, Italy, for the European Championship - and he didn't need a second invite.
His frequency of trips to Auckland became a fortnightly affair where he sponged off everything coach Frankie Lardies disseminated, indebted to those who made it possible to book flights and billet him.
It hardly mattered that Gilmore finished 80th out of a fleet of 160 in an overseas regatta that lured pedigree sailors from outside Europe.
Again, it was a revelation to see other 13-year-olds who were in a different league, not just in the water but off it, too.
"The kids did everything, including tying up the boat. The coaches didn't bother with them so it was all at a different level," says father Kent, noting the parents of those youngsters had more resources "at an entry level" than him and wife Carla.
Perhaps the other thing that struck them, even in Auckland, was that more than 25 youngsters turned out for practising whereas in Napier Gilmore had just club mate Jordan Daikin, who is ranked No47, to push each other.
Seventy-seven entries have been received in the green fleet championship, which is for the up-and-coming open fleet sailors.
Several elite optimist sailors from the country are vying for a place in the national team for the world championship to be staged in Malaysia at the Royal Varuna Yacht Club, near Bangkok, in July.
Gilmore, whose dream is to be among the Team New Zealand crew in the America's Cup campaign, thanks his sponsors Thirsty Whale and Ocean Spa gym, for the opportunity to take advantage of conditions in his backyard.
"I reckon I can totally achieve it. There's no reason for me not to dwell as I've got all the skills," says the sailor who has made lifelong friends along the way.
After the regatta, he intends to take it to the next level, starlings, next year and the two-person skiff 29er dinghy before venturing into the 49er class. Going abroad will help broaden his horizon but Gilmore, who will be in the school team mix, believes it's do-able within the country as well.
