To put it in perspective, last Saturday he covered 103km, soaring to heights of 5500 feet above sea level and flirting with the 60kmh mark downwind although he covered 185.1km, if you take into account the thermals (catching updrafts of rising warm air towards the sky in a spiralling circular motion akin to birds such as hawks and falcons).
However, Gilbert's longest journey was about 125km in the Manawatu coastal side almost a decade ago.
His thermal circles are deliberate because in the absence of a motor-less craft, with just a parachute above his head, he has to maintain his altitude because for every 10m he advances he drops a metre.
"I can't make myself go up because I'm always going down, unless the air's going up faster than I'm coming down so those areas of lifts are called thermals."
Gilbert says the cauliflowered-aired "head jobs" of cumulus clouds are evidence of thermal activity so he hovers under those air mass to hook into some a little earlier in their life cycles, ideally between 500 to 3000 feet.
"That's one of the many skills involved with this sport," he says, dispelling any preconceived notions that a pilot plays a passive role.
If anything, the pilot has to be not only in harmony with nature but comprehend it enough to be able to dictate terms.
Gilbert reveals there are three grades of pilot — PG1 (beginner), PG2 (intermediate) and PG3 (advance) rating, which is what he his.
"Within that involves understanding all the air space in New Zealand which is controlled by the civil aviation authority because they carve up all the space into different areas."
For instance, the coastal region around the Hawke's Bay Airport in Napier has its limitations.
"Imagine an upside down wedding cake — so as you get away from the airport you're allowed to get higher without infringing in their controlled air space."
He takes a Garmin inReach electronic device that enables him to messenger someone, via satellite network, if he drifts outside a cellphone range should he find himself in a spot of bother — something he has yet to experience.
"I can also simply press an SOS button which links to a 111 emergency call where they'll have my co-ordinates and can track me.
"It was a good chance to get to Waipuk and the day turned into something quite special so eked out everything I could out of it."
He laughs when asked if there's a support crew waiting for him at the end of his spontaneous journey.
"That'd be nice, eh. Nah, I land and hitch hike back again."
Thankfully his paraglider compresses and folds into a compact-sized unit which he chucks into his backpack.
"I've always got home," he says. "That's where the magic is."
The launch from the 900-feet altitude at Te Mata Peak is technically challenging but so is the landing.
"Coming back from a flight I've met some of the most amazing people."
Most people tend to be gobsmacked watching him walk up with his back pack sceptical about his unannounced arrival.
"They don't see me land and just see me walking up to their house so wonder what's going on."
He suspects they often wonder if he's rustling sheep or cattle but when he enlightens them, very carefully, the eyes of the property owners tend to light up.
"People are excited by other people who, you know, are going for it so it's a wonderful thing."
Without fail that unexpected meeting turns into typical countryside hospitality amid suggestions a neighbour may be heading to town or a passing school bus will give him a lift to the next stop.
"People really go out of their way to help you," he says, lapping up invites for an uplifting cup of tea and snacks.
Gilbert is often conscious of smartly cutting a track "towards some form of civilisation" so he can be back home again.
He buys into the philosophy that he'll push the boundaries of gliding but sensibly tucks into his aircraft a sleeping bag and some food, such as muesli.
"I know I'll find somewhere to sleep for the night — in a hay barn or wherever."
So far, in his paragliding pursuits since 1989, he hasn't had to rough it out overnight.
Then there's the unrehearsed chapters with motorists in a rash of hitchhiking rides back.
"Some of them aren't remotely interested in what you've done or where you've been. They seem more interested in sharing their problems and woes."
However, there are some who do ask and engage in deep conversations about the pros and cons of paragliding.
"I don't care whether it's about me or about them because it's always interesting conversations with lovely people."
In the scale of wing class, with A providing stability for an easy flight, he uses D-class wings for efficient long hauls.
He engages in an online, year-long cross-country competition against other enthusiasts in New Zealand. They record their flight paths digitally and submit them to a website where it's collated and made accessible for others to peruse.
"It's not something that happens on a per-day basis but over a long period."
Gilbert says not too many pilots have covered his distance in the North Island except a strong group based outside the Wanaka and Queenstown region in Central Otago.
Nick Neynens, of Glenorchy, a meteorology student studying in Australia, occasionally clocked 200km-plus flights and has a penchant for competing overseas.
Okay here's the burning question — what if nature calls during flights?
"I've got a little catheter which runs down my leg and I hang it by the side of the ... and, yeah, I pee ... and it falls away all around my face.
"This is the first year I've used it and it takes so much pressure of me."
Gilbert often glides with his son, Mark, 14, who recently elected to make an emergency pitstop at the Porangahou home of Gilbert's sister so it pays to have some geographic sense, too.
What grabs the senior Gilbert is how dynamic a sport paragliding is because every flight offers edification although it can be just as frustrating a code as cricket in summer, which is at the mercy of inclement weather.
"There are no stories and there are endless stories to share, if you know what I mean. You know, I can go on forever but there's nothing I can see that stands out as, 'Wow, here's a show stopper'.
"It's just a whole lot of cumulative stuff that has proven to become magic over the years."
The growth of the sport is reflected in how the Hang Gliding and Paragliding Association has infiltrated various parts of New Zealand.
The electronic age and social media have worked as catalysts in breaking down barriers to enable enthusiasts to engage even internationally.
The Bay branch has about 30 members but its roots beginning here makes Gilbert chuckle.
The New Zealand Hang Gliding Association got the concept off the launching platform until the early 1990s when paragliding pilots started emerging.
When he first came to the Bay from his big OE in 1990 he was allowed to attend club meetings but his contribution was minimal — sit in the back and please don't say anything — as the sole paragliding pilot among hang gliders.
"Now we have one hang glider pilot and the rest are paragliding ones so you can imagine the dynamics."
He puts the transformation from hang gliding to paragliding purely down to the logistics of the former demanding cars, roof racks and a yard to rig the glider and a support crew to help you launch.
"When you land you've got to have somebody hitch back to the car and take it to the driver so there are a whole lot of things.
"With the paraglider you walk up and two minutes later you're ready to launch. When you're finish it's in a backpack and that's the end of it."
He feels the performance advantage of a hang glider is marginally superior but not enough to negate the need of all the other hassles such as dismantling aluminium bars.
Gilbert equates the therapeutic benefits of paragliding to yoga.
"When you're in the sky you're completely focused on where the next lift is going to be and how the paraglider is responding.
"If you take your mind off the job then you'll end up walking so you have to be in tune with what's going on around you to stay airborne."
He finds it physically relaxing but mentally stimulating and challenging.
Before paragliding Gilbert found traction and immense satisfaction in kayaking in Taranaki where rain springs eternal waterways and tributaries.
When kayaking started becoming extreme negotiating bushland to paddle off Mt Egmont he had to look outside the risk factors.
"The writing was on the wall [because] sooner or later I was going to get pinned under a rock and it was going to end badly so I was looking for a new challenge that wasn't going to be as risky."
The article of a magazine scribe, Bev Smith, on flying off Mt Ruapehu had not only caught his eye but his imagination.
"I thought what a fantastic thing," he says, preferring to see his penchant for such activities as individual sports rather than extreme sports.
"I suppose it's extreme in a lot of people's minds but I don't see it as that but just understanding what the sky's doing, how it's doing it and how the winds reacting so it's like a good driver on the road who can eke out the most performance from a machine."
Like his son, daughter Amy, 16, also attending Taikura Rudolf Steiner School in Hastings, has a licence to glide as well.
The concept of family members taking a shine to paragliding appeals to Gilbert but he emphasises it's "a very individual sport".
"As you'll well appreciate there aren't 100,000 paragliding pilots in Hawke's Bay but just 30 of us of which probably only three or four who are at the level to venture out to the countryside."
