"It's to get the guys out of their own world, and to take them to places they wouldn't normally fly," he said.
"I do all the organising, and find neat spots around New Zealand for them to land. Plus, they get to hang out with like-minded people."
The tour group consists of about 25 people, part of an informal liaison of helicopter enthusiasts, who range from student fliers to experienced pilots with their own choppers.
On the most recent tour, they visited Waitomo, where they went caving, then flew over Raetihi and landed at Castlepoint Lighthouse.
Mr Crane said they are the only helicopter tours of their kind being organised in New Zealand.
"There's some guys in Australia who do something similar, but I think we're the only other ones in the Southern Hemisphere," he said.
"It's a shame that a lot more people don't do it. We have a lot of fun - I fly with a neat bunch of guys."
Part of their trip to Masterton included a tour of the Hangar of the Old Stick and Rudder Company, which houses a rare collection of airworthy WWI aircraft.
Mr Crane said he hopes to bring tour groups to Wairarapa more often.
"Wairarapa is such a beautiful area - it's neat to fly over."