Constitution Dock, Hobart December 29 1975

I saw the owner and skipper of Kialoa III, Jim Kilroy, heading towards me with his crew. He was on a high, having won and set a race record that would stand for 21 years.

I just happened to have a beautiful backlit picture of his boat planing at 23 knots off Maria Island. I showed him the print, and he didn’t need to think about it for long.

“I’ll take that one in the largest size you’ve got (20 inches by 16 inches – what we’d call A2 these days). How many in the crew, 22? Okay, we’ll take 23 of those.”

They were $35 each at a time when the average weekly wage in Australia was $146.

Then the owner of the second-placed Windward Passage showed up and placed a similar order. Some of the crew bought ten copies for themselves in the same size. I sold somewhere between 60 and 80 of those two boats alone.

At that moment, I realised I had a new career.

Kialoa iii

Kialoa on the way to breaking the race record of 2 days, 14 hours, 36 minutes and 56 seconds. The record stood for 21 years.

windward passage

Windward Passage was 20 minutes behind Kialoa. This photograph was recently featured on the front cover of Wooden Boat Magazine.

And so it began, but in truth, everything that went before had been leading up to this moment. A daring mountaineer and tireless trekker, Richard fused his love and skill of photography with his fearless, adventurous spirit, 400 feet above the Sydney Hobart yachts in a tiny Cessna 172.

In the 50 or so years that have passed, the aircraft he shoots from and the equipment he uses may have changed, but his ability to tell the story of a yacht’s race in a single frame has remained.

It’s a rare skill, bolstered by a resilient passion. Artistry and tenacity in equal measure. Richard’s pictures take us to places that we could never go ourselves and show us moments and memories that would otherwise be lost to time. Chasing boats across white-flecked water canyons; battling weather and improbable odds. Richard shares all of this generously on this website.

His annual quest to capture drama and achievement are gathered here; the gems unearthed in his never-ending search for perfect light and shade are yours to enjoy and own.

shooting from the aero commander

Photographing the Sydney to Hobart Yacht Race circa 1994.

on tasman island waiting for the boats

Richard now photographs the yacht race from a helicopter. This portrait was taken in 2020 by his daughter Alice Bennett.

Indian Ocean

63 DAYS IN THE INDIAN OCEAN — AN ADVENTURE TO (ALMOST) END ALL ADVENTURES

Richard’s adventure, so far

the fearless pursuit of extraordinary endeavour has taken richard to places few have been.

Member of the first Australian Andean Expedition 1969 including 5 first ascents
60 years exploring Tasmania’s wilderness on foot, including 48 South Coast Tracks and 12 summits of Federation Peak
48 consecutive Sydney Hobart Races
Nikon-Kodak Australian Press Photographer of the Year Award,1999, for ‘Best Sports Photograph’
Photo Imaging Council of Australia, Gold Tripod Award for outstanding contribution to the Australian imaging industry
Eisenstadt Awards for Press Photography, New York, Finalist 1999
Australian Institute of Professional Photography: Master of Photography; Fellow of the Institute; Past President; Chairman, Australian Professional Photography Awards
Centenary Medal for promoting Tasmania through photography
Order of Australia for services to photography

Stuart McGregor, bushwalking companion and friend.

“Through adventure and exploration, Richard’s photography embodies his joy of the natural world, whether it is by tackling the high seas, scaling mountains, trekking through valleys or just camping out. His thoughtful contemplation, expressed in his images and words, delight and inspire.”

In the action

SYDNEY TO HOBART – IN THE AIR, PHOTOGRAPHING THE WORLD’S TOUGHEST OCEAN RACE