Kai Lenny

Kai Lenny’s entire parawing record fits in one clip. Maui’s best-known multi-discipline waterman was filmed combining a parawing with a SUP longboard at Hookipa: parawing to build speed into the wave, stash, then surf the wave hands-free. One documented session, and it still earns a profile, because it shows the sport’s crossover ceiling better than any race result would.

What the Hookipa session showed

Deploy, power up, use the canopy as wave entry instead of paddling, then stash and surf clean. That’s the core parawing pattern, applied here to a board with no foil under it. Duotone’s Jeffrey Spencer describes the same pattern on their gear: “The best part about the Stash is packing it mid-session and just riding — no wing in your hands… When powered, it gets you on waves early and makes going upwind way easier than paddling” (Duotone). Lenny’s demo made the point that none of this is foil-specific. A parawing can be a compact, stashable engine for any wave craft. The foil version of that skill set lives in wave-riding sequences and stashing mid-ride.

Maui matters here. The modern parawing was invented on that island. Greg Drexler’s Maliko V1 launched August 21, 2024 (The Inertia), and by 2025 Paddle Imua ran the first-ever parawing race division on the ~9-mile Maliko Gulch–Kanaha run, back on July 12, 2026 as part of the Koa Kai Triple Crown. When the island’s most famous waterman picks the tool up, even for a single filmed session, that says something about where the discipline can go. See the Maliko run profile for that stretch of water.

Is Kai Lenny a parawing racer?

No. He does not appear in the published 2026 SFT Downwind Parawing rankings, and there’s no record of him entering a tour stage. File him under freeride and crossover icons, not racers. The competitive field is covered elsewhere in the riders section.

Two caveats. First, no published quotes from Lenny himself about parawinging have surfaced; every quote on this page comes from other riders describing the same technique, each attributed by name. Second, the session is not an invitation to copy it. Hookipa is a breaking-wave spot, and standard parawing safety guidance (Duotone, among others) says stay out of breaking waves because of line-tangle hazard. A doused canopy plus whitewater plus bridles is a bad place to be for anyone without his water time.

What the clip does establish: the parawing’s endgame runs wider than downwind racing. It is paddle replacement, wave-entry engine and self-storing power source in one, with the crossover experiments only starting. If you want to chase that yourself, practice the stash on flat water first, and know what a tangle recovery looks like before you take a parawing anywhere near surf.