Surfing Downwind: The Molokai-to-Oahu Race

During the annual Molokai-to-Oahu race, top downwind surfers gather to paddle from Molokai to Oahu via the Kiawi channel. Cheer the competitors on at the finish line in Hawaii Kai on Oahu. 

Text by Anna Harmon
Image by Morgan Hoesterey

Hawai‘i has always been a land of watermen and women, perhaps most well known for being the birthplace of surfing, where ali‘i, ancient Hawaiian chiefs, danced atop the foamy seas. Despite surfing’s celebrated history, it was downwind surfing that brought the ali‘i here in the first place, paddling hundreds of miles on outrigger canoes from Polynesia.

Downwind surfing requires tradewinds and open-ocean swells and can be done with multiple-person or solo canoes, kayaks, or stand-up paddleboards.

To leave the beach behind and risk losing your vessel to rogue waves or squalls takes guts. It’s a sport that demands real respect, even if it doesn’t draw huge crowds and sponsors. For the folks who do it, this is perfect. It leaves them space to roam.

“Just picture you’re looking at Diamond Head right now, then you look out past the surf and see the wind blowing all those little white caps all over the place,” says North Shore lifeguard and downwind surf fanatic Kirk Ziegler. “If you were to paddle against it, the wind would be blowing in your ear and in your face. … Then you turn around and it’s quiet, because the wind’s on your back. You don’t see the white caps anymore; you just see a wave to your left, a wave to your right, a wave in front of you, and you just paddle in.”

Hawai‘i’s downwind surfers, as well as those around the country, can travel the islands to compete in various races that take place every year, such as the Kaiwi Channel, a 26-mile water path that stretches from Moloka‘i to O‘ahu.

But while races offer recognition of skills honed and training paid off, the majority of downwind surfers in Hawai‘i don’t do it for glory; they do it to get intimate with the signature tradewinds, challenging waves, ocean tradition, and scenic views of the place they call home.