"I think I can do it," he says of a ride which will be monitored by wife Lizzie in what he describes as his "broom wagon", a cycling term for vehicles which sweep up stragglers.
"It's my biggest day on the bike. I've just got to keep pedalling.
"I'm on a TT [time trial rather than climbing] bike, and it's safe to say I've seen no other TT bikes up any of these mountains. I get a few weird looks and comments, but it's all about getting the power out of that position on the bike.
"It's a bit like taking a Formula One car on a rally. Working those [optimum TT] muscles while fighting gravity should make for a good strength training block."
Bond's meticulous preparation is an endearing but obsessive quality which made him one of the greatest rowers of any era.
He has applied the same modus operandi to cycling as he attempts to squish knowledge normally built over a generation into a four-year tilt at the Tokyo Olympics.
A New Zealand Olympian qualifying in two sports is a rarity - Steven Ferguson (swimming and canoeing), Madonna Harris (cycling and cross-country skiing) and Chris Nicholson (cycling and speed skating) are examples. None earned medals.
To give a global context, 81 athletes have secured medals in separate Olympic sports, but only 14 came post-World War II and four were this century.
Of the latter four, only one came in a transition between two summer sports. Britain's Rebecca Romero went from a silver in rowing's quadruple sculls at Athens to a gold in cycling's individual pursuit at Beijing.
Bond accepts he is attempting to reach rarefied air.
"I'll need a wheelbarrow to carry all my ideas back on the plane [on August 7] but I've still got expert resources to tap into like Dr Xavier Disley of AeroCoach, who understands what I'm trying to achieve.
"A week after I arrived, I did a testing session with them which improved my positioning and equipment, saving several watts of power. I've since tried to bed in the changes and have another testing session in a couple of weeks.
"I'm getting confidence from my results which show I'm not too far off the realm of world-renowned time-trialers. But sometimes you flip that around and ask 'what the hell am I doing?' Doubt creeps in. I'm not sure if this is the biggest challenge I've had, but it's the biggest step into the unknown. I ask myself 'why do I think I can compete with these people who have tried to do this their whole careers?'"
He's settled on an answer.
"I'll just do it to the best of my ability and wherever I end up, I'll be satisfied, as long as I feel like I've done it justice.
"That's how I balance out the expectation and the daunting task of getting to the top level, which is readily apparent when you watch the Tour de France.
"I watched [four-time world time trial champion] Tony Martin going up a hill [in the Pyrenees] and if I get to where I want, that's the type of guy I'd have to race."
He also observed George Bennett, who is becoming a contender to deliver New Zealand's best general classification finish in Le Tour.
"I sent him a message that I'd be out on the road. He said 'give me a yell', so I did, and he turned his head. I hope he heard me because he's doing an amazing job.
"Seeing the whole [Tour de France] roadshow for the first time is something else.
"There's a long way to go, but to survive and hold his own with the best in the world is pretty cool."
Bond's experiment has required some logistical masterstrokes. He packed his life into a van which The A-Team would be proud to call their office, and experienced complimentary hospitality throughout Britain courtesy of their rowing community.
"I've had a backlog of invites and offers of places to train and stay. My van has covered 3000 miles criss-crossing the country. I've never had to sleep in it, so that's a win.
"I'd get to races with the bike strapped to walls and everything in its right place. Then I'd set-up like a rowing tent out the back door, chuck the keys on a tyre while I raced, and return exhausted.
"I'd be keen to hit the road, so everything would get biffed in and end up a complete bomb site at the next stop."
Bond began his tour with victory in the 10-mile Greatham Handicap on a blustery evening at rush hour along the A3 dual carriageway south of London, an experience he likens to pedaling the Waikato Expressway.
He repeated the task a week later, humming at an average 53.88km/h to record 17m 55s. That beat the course record, as well as London Olympic champion Sir Bradley Wiggins' best over the distance.
Bond has two more races in Britain as his pioneering vision continues.
"It's a case of nothing ventured, became a situation where I was doing it for results in the end. This flips it around because the results are so uncertain that if you don't enjoy the process, there'd be no point."
