Jamie O'Brien: the sexy windsurfing experience with Kai Lenny

Jamie O'Brien decided to go windsurfing with Kai Lenny for the first time. The result is a beach wipeout.

The iconic and innovative Pipeline master has never been a man of wind sports.

Kai Lenny enjoys surfing, stand-up paddleboarding, windsurfing, and even kitesurfing, so he invites O'Brien to a waterman's day.

Maui was the right place for Jamie O'Brien's first windsurfing experience. The baptism got underway in windy conditions, but before sailing time, both riders went out for a SUP train.

Soon after, Jamie O'Brien was laughing about the long windsurf fin, the need for a harness, the sail, and the mast.

What's this for? Kai wanted to help, but it wouldn't be easy.

In the first few seconds of tandem windsurfing, Jamie falls. One, two, three, several times.

Minutes later, they were both sailing well, always together and under Lenny's surveillance. Not bad.

In the dying seconds of the windsurfing experience, Kai decides to sail as fast as he can towards the beach, leaving poor old Jamie alone in a sand crash accident.

Impressive stunt. Will Jamie O'Brien ever get back to windsurfing?

Top Stories

It's official. The World Sailing Speed Record Council (WSSRC) ratified two new outstanding accomplishments in windsurfing and kiteboarding.

Professional surfers Kai Lenny and Jamie O'Brien embarked on a thrilling adventure when they set sail aboard the high-performance USA SailGP F50 foiling catamaran.

Planing is one of the most exciting skills you can master while windsurfing. It usually separates beginners from intermediate and advanced sailors. But what is the minimum wind speed to get flying over water?

Imagine gliding across a frozen lake, your sail catching the wind, and skis slicing through the ice and snow. Meet the sport that blends the thrill of windsurfing with the crisp, cold beauty of winter landscapes.