No one is pushing the possibilities of hydrofoils more than 24-year-old Kai Lenny. Since he began riding them on open ocean swells, Lenny has ridden a foil board in rivers, across Hawaiian channels and even in New York.

“Now that I’ve pushed myself by myself so many times, the next challenge would be to see how I compare to another craft,” Lenny says in the below video. “Challenging myself to a sailboat would be cool.”

And who better to race in a race than world champion surfer and big-time sailor John Florence?

Lenny and Florence have a brief race, and determine a wager: if Lenny wins, he gets the boat. If he falls, Florence is leaving him behind. While a winner isn’t quite determined, we’re guessing Florence didn’t have to give up his sailboat to Lenny, and that if Lenny did fall, Florence came back to get him.

Clearly, riding open ocean swells by himself was only just the beginning for Lenny and his hydrofoil pursuits.

Kai Lenny and John Florence laying down the terms of the friendly wager.

More about Kai Lenny from GrindTV

Only Kai Lenny would hydrofoil in New York summer flatness

5 of Kai Lenny's greatest recent feats

Kai Lenny adds hydrofoil to boogie board to create boogie foil