Sometimes as many as four planes will fly in formation for up to 10 minutes, while he uses hand signals to direct the pilots into position.
But he says the somewhat precarious nature of the job doesn't bother him at all.
"Usually it's very beautiful. Usually it's exciting and wonderful, I'm never afraid - there's no fear involved. I fly with some of the greatest pilots in the world.
"I'm very lucky to fly with these boys."
One of the challenges of the job is being subject to so many forces beyond his control, he says.
"I'm an observer - I'm not in control of what happens - you go up if the weather allows. If the weather allows, you go up if the motors start, and often they don't.
"You fly at the mercy of circumstances and if you are lucky, you are lucky."
Since arriving in Masterton last Wednesday, he has flown nine flights and taken about 2500 photographs.
For every 200 shots, one photograph might make the cut. For him, capturing those "miraculous" moments is what it's all about.
"When these planes come up it's dazzling. It's very beautiful. The real excitement is when something really wonderful happens - when some miraculous event happens - which is quite frequent.
"I guess I'm addicted to the miraculous."
Mr Makanna, who hails from San Francisco, travels the world sourcing images for his calendars, and says the Masterton collection rates among the best in the world.
]"These boys are wonderful and these planes are totally unique. There's no place in the world that has so many historic World War I airplanes. It's a brilliant collection."
