The Rise of Wing Sailing

The latest watersports craze is getting more people on the water and harnessing the wind.
Young rider Kainani Drexler is one of many new converts to wing-foiling. Scott Drexler Photography

On a family cruise this past summer, our girls, always on the lookout for something interesting, spotted four tiny colored blots hovering around a 70-foot motoryacht plowing along downwind in a blustery sea breeze. The colors would disappear in the yacht’s wake, in and out, until they turned and started heading toward us. As they got closer, I recognized four inflatable, polyester-skinned mini wings, no more than 9 feet in span. A bunch of dudes in wetsuits riding foil boards were flying along over the wave tops, hunting “bumps” (short surfs) and longer rides on the wakes of passing boats. They’d catch a surf and float the wing at waist level with one hand while they carved the wake. Then, in a blink, they’d turn upwind with the great ­pointing ability that foils provide. Never mind the girls’ excitement; I put two and two together and thought, Now that solves a lot of problems.

Foiling, now in its many ­facets, has cracked open the wind-sport world, and sailors, windsurfers and kiters are embracing everything new, riding in more places, in less wind and at higher speeds. But there has always been ­nagging ­issues with equipment: Foiling ­dinghies need dollies and endless ­maintenance, and require hiking. If the wind dies, you’re toast. Kites need a lot of open space to launch and land, and once you’re off the beach, there’s no stopping.

Wing-foiling has no such issues. The wing is simple, small and portable, and can be used on a variety of boards, big and small, foil or not. At the moment, there’s no formal ­racing—channel crossings are the cool thing to do, and when you need a break, you can simply float on your wing like a pool float and chill between rides.


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It’s not surprising, therefore, that wing-foiling, wing-­surfing or whatever you’d like to call it, has arrived. Big time. In 2020, wing distributors around the world can’t keep up with demand. If you want a wing and a high-volume wing-foil board right now, good luck.

Today, it’s impossible to breathe the words “wing” and “foiling” without conjuring up images of professional ­athlete Kai Lenny flying off the lip of a Maui wave, wing held high overhead, or Robby Naish’s silly and fun GoPro tutorials online. These giants of wind and wave sports got on the wing thing immediately, and much of the current popularity can be attributed to their videos alone. Unlike modern windsurfing and kiting, however, winging has nothing to do with competing—for now, at least. It’s all about freeriding. Naish is just playing around. Lenny is cruising the open ocean with his buddies. And, most important, kids are getting into the act, doing what they do best, using social media to make winging cool. It helps that wing sailing, whether on a stand-up paddleboard without foils or a high-priced foil board, is easier to learn than foil ­windsurfing or kite-foiling.


Alongside icons Lenny and Naish in the wing world are groms Kainani Drexler and Bobo Gallagher. Watching these two middle schoolers hit bumps and boost airs in their loose and playful online videos is infectious. “Growing up, I was the only female grom, and there haven’t been that many girls who wing-foil,” says Kainani, who started kiteboarding at 7. Kainani says old-school twin-tip kiting is “pushing water” and slow. She went straight into kite-­foiling. She got a simple foil with only a 12-inch mast—the vertical part of the foil—from her uncle, Greg Drexler, a developer of wings, kites and foil boards. She kited with that for about a year, and when her uncle started to make wings, she made the switch. “A lot of people are getting into it. There are more women. They think it’s safer [than kiting or windsurfing]. I think it’s for everyone, especially kids. Lots of kids think it’s cool to keep it flying, with the wind pushing.”

Unlike modern windsurfing and kiting, however, winging has nothing to do with competing—for now, at least. It’s all about freeriding.

It’s not just kids getting into it either. “Winging is exploding, and what’s interesting is it’s not the normal customer base,” says Philip Mann, owner of Inland Sea Windsurf Co., on Cape Cod. “Now it’s ­people ­coming from little to no ­background in watersports.”

Mann, who has been in the windsurfing industry for 25 years, says that the ease of use is what sets winging apart from windsurfing and kitesurfing. “There’s not much to teach. A lot of it is trial and error. It’s more intuitive, and people perceive it as safer.” He says the learning curve on the foil takes time.


The equipment Mann recommends for beginners includes an inflatable wing. Some models have a small “boom” that windsurfers prefer. Others have handles on an inflatable center strut. Lighter wings with shorter spans are better for kids and smaller adults, and windows are a good idea, even though you can raise the wing to look around. High-performance wings have been used for ice and snow sailing for years, and while the new inflatable wings are more recreational than high-speed (for the moment), outright ­performance isn’t the point.

Beginner boards start at around 5 feet and have higher volume to support the rider standing, like an SUP, before powering the wing. Foils come straight out of surf foil world, with large area, high-lift ­forward foils and short masts, so crashes aren’t as dramatic.

“You can do this on the Mississippi River,” says Mann, who adds that it doesn’t have to be just foiling with the wing. “The fun part is going out and having a good time. We are now seeing people strapping daggerboards to their SUP [to prevent leeway]. The market always focuses on lighter and faster. That’s what hurt ­windsurfing—they stopped ­filling in behind with beginners.”


Wing-foiling is now the most accessible form of foiling, in terms of practicality. At the Olympic classes world ­championships in Melbourne, Australia, this past winter, there were coaches who traveled with their wing-foilers. After their debriefs, they’d launch and buzz the harbor, stretching their minds and learning more about foiling. “It’s really the only sailing I can do to get exercise and bring it with me,” says Jo Aleh, a gold medalist and coach from New Zealand. “Getting into ­foiling helps too.”

With inflatable boards now available, a complete kit can fit into two duffel bags. Cost is a bit prohibitive, with the wing, board and foil each costing close to $1,000, but cost doesn’t seem to be deterring newcomers. “Our harbor (Kahului Harbor) never had people sailing in it, now everybody’s doing it,” Kainani says. The average day there now has 20 to 30 people learning. Kainani and her father spent a recent 25-knot day at Kahului teaching three other girls and their mother for hours. Then they went to the other side of the island, and Kainani worked on her cutbacks and bottom turns in the steep waves. Downwind and bumps are her jam right now.

“There are already substantially more kids wing-surfing here on Maui than either kiting or windsurfing, and the number is growing by the day,” Naish says. “There is no better way to foil. It is the least expensive form of foil sailing, it is very easy to learn, and it offers an incredibly direct and amazingly fun sailing experience. It is substantially easier and more direct than either wind-foiling or ­kite-foiling. This will be the ­foil-racing craft of the future.”

Foiling has been about going faster with less—less equipment, less effort, less wind—and all that adds up to fun. I recently bought one myself, and watching my young daughters laughing, running and jumping with a 4.0 wing, and then reaching around with it on the SUP is a thrill. They’ll probably soon surpass my abilities on the foil and be chasing down bumps in our backyard, and I’m cool with that. They spotted it first, so it’s only fair.