FORT MYERS WATERMAN
Roy Massey has mastered the art of riding the wind and waves of the Gulf of Mexico. He's ready to share everything he knows.
Roy Massey has mastered kitesurfing, paddleboarding, windsurfing and more. The expert talks about the world of water sports and why Southwest Florida is the best place to do them all.
“There are bad addictions, and there are good addictions—and this is definitely a good addiction,” says Roy Massey of the waterman lifestyle, which, for him, means a daily fix of the Gulf of Me xico and its myriad inlets and bays.
The 55-year-old owner and operator of Ace Performer, a water-sports retail shop and instruction hub in Fort Myers, feeds his habit with a mix of kayaking, paddleboarding, windsurfing and kitesurfing, all depending on how the wind is blowing—literally.
“When it’s cold-front season, like yesterday, it gets windy and all my kitesurfing and windsurfing friends show up,” says the tall and lean blond. “The opposite is true with paddleboarders and kayakers. They don’t like the winds. When it’s blowing 15 to 20 mph, they get blown all over the place.”
Either way, Massey joins in. He brings different gear, but the resulting spark of pleasure is the same.
Hearing the excitement in Massey’s voice is an invitation, an easy gateway to joining him in his passions. It’s hard to listen to him without getting curious and perhaps even ready to try a new hobby.
To pick up a kayak or board, there are almost no limitations, even and especially age.
“I have friends who are 80, 84 and older out on the water. The oldest guy I know who windsurfs is 90, and the oldest guy out here who kitesurfs is 75. It’s amazing to see people that age out on the water,” he says.
One of his favorite couples is Maggie and Mike, both in their 80s. Together, they play tennis most mornings and windsurf most afternoons. “That’s crazy! They’re doing it all,” he says.
How they came to like a water sports-addicted lifestyle is how it starts for most folks.
“People come down here and retire. These are some really healthy people. They come into my shop and ask, ‘I can play tennis and golf, so can I windsurf? Can I kitesurf?’”
And the answer is always the same: “If you still have your brains and your body, I can teach you.”
As soon as people express that interest, Massey launches them on the water as fast as he can. That’s why he strategically placed his shop on McGregor Boulevard, close to the Sanibel Causeway.
That patch of San Carlos Bay paradise is one few know as well as Massey, a Fort Myers native.
As a kid, his father would bring him to the causeway to canoe and kayak. Years later, at age 19, Massey started windsurfing and realized how perfect the Sanibel Causeway is for wind sports. “You have to go where the wind blows on shore,” he says of what makes for an ideal windsurfing or kitesurfing spot.
His longtime customer and colleague Robert Page Henderson also treasures the location. “It’s all about access. No matter which way the wind is blowing, you can find a good launch along the causeway.”
He adds that along the second island of the causeway, “when conditions are just right—it needs to be the last hour before low tide and with an easterly wind—it is just the berries. You can get on the backsides of the waves and ride the wave face without ever having to get back to windward.” In other words, it’s endless cruising.
Of course, Massey ventures beyond the causeway, especially on his days off. His preferred spots are the same ones he steers his clientele to.
“All of the bird refuges, like the J.N. ‘Ding’ Darling Wildlife Refuge, are great because you can’t use a motor.” Which means that nonmotorized boats have a monopoly. “You don’t have to worry about a Jet Ski motoring through and scaring all the birds
and fish away. The fishermen love that.”
Another of Massey’s favorite spots is Bunche Beach Preserve, a five-minute drive south from his shop. Really, anywhere with shallow water, ideally just three or four inches deep, you’re likely to find Massey and his people.
“With places like that, nothing but a paddleboard or a kayak can have access. You’ll find spots like that all over the back bay of Sanibel and Pine Island.”
Another favorite is Turner Beach, just past the bridge connecting Sanibel to Captiva.
If any of these areas seem too great a distance to paddle or sail to, rest easy knowing there is a cheat. Many people take their powerboats as close as they can to a protected area, then they go paddle and explore from there. They may go to fish. Many go simply to witness the dolphins, osprey and sea turtles. Plus, for many paddlers and boarders, being on the water is the best stress therapy there is.
If you are new to water sports, how do you know where to begin? “Everybody is different,” says Massey of each person’s starting point after walking into his shop. “Some people have never been on the water much, and they typically start with kayaking. See if you like that. Then, you can stand up and paddle, so you get more of a workout. Plus, you see a lot more. If you can paddleboard, I can get you to windsurf in an hour. Windsurfing is the same workout as paddleboarding, but using the wind.” To move onto kitesurfing, the next step is learning the kite-flying skills. For Massey, it’s a natural and easy progression, one that he understands clearly, thanks to decades of experience with every sport he teaches. Teaching comes naturally to Massey, and it’s a source of constant inspiration for him. “That’s what I like most about teaching—getting people on the water who thought they would never be able to windsurf or kitesurf.” Though now a big part of his day to day, teaching isn’t where Massey thought he would be when he started his business in 1986, shortly after graduating from Edison College (now Florida Southwestern State). At that time his sole endeavor
was crafting boards. From a warehouse in Fort Myers, he shaped windsurfing boards, skimboards and surfboards. That lasted until 1995. “I realized I couldn’t make enough money to stay alive by just building boards, and so I moved into teaching and getting more people on the water. I was trying to do everything, and it just didn’t work.”
Now, he isn’t just getting by—he’s thriving in that sweet spot of joy-meets-passion.
One of the unique benefits of coming to Massey for instruction is that he’s able to match up a newcomer with the sport that’s going to be the best fit. He knows which questions to ask, and how to build confidence in newer enthusiasts so that they stick with the sports they’re drawn to.
Between windsurfing and kitesurfing, Massey says, “I tell most people to get into windsurfing first. Kitesurfing has a longer waiting period between learning and actually riding.”
Plus, windsurfing is possible under a wider array of wind conditions.
“To kitesurf, you need at least 10 mph, otherwise you are just swimming,” Massey says, laughing the easy chuckle of a guy who’s been there and seen it all.
And he has tried it all—and mastered it all—but hasn’t forgotten his early days. The memories keep him humble, and keep the reminders fresh as to what not to do. “Oh yeah, I got dragged across the beach a couple times when I was learning to kitesurf, but nothing serious.”
In his teaching he always stresses the importance of safety systems. For windsurfing, should riders feel in danger, they need only to let go of their sails. For kitesurfers, it’s a bit more complicated.
“You need to know where your safety systems are, so if you’re by a bridge or a tree or anything hard, you can pull that quick release,” he says, referring to the system that depowers the kite—releasing the tension that keeps the kite flying. Hit the release, and you’ll stop being pulled, and the kite drops to the water.
It’s certainly the biggest lesson Massey emphasizes when teaching newbies to fly.
As much as Massey sees the value in safety, so, too, does he see the value of connection. Of community. The work he does isn’t just about selling boards or rash guards. It’s about helping people make new friends and about giving families new experiences to bond over.
“I’ve had grandparents come out with their kids. I get whole families up and windsurfing in an hour. That’s really cool to teach several generations at once. And that’s so cool for them that they all share in the first time they windsurf together.”
Massey places no age restrictions on older enthusiasts seeking lessons, but he does limit the age of kids. “I don’t recommend teaching kids until they’re 8. Before that age, they don’t have the attention span, strength or stamina. They just don’t understand the concepts.”
Younger kids need not miss out, however. In his for-sale and rental fleet, Massey stocks lots of “big, floaty boards that you can put the whole family on.”
Though his own kids are in college now, when they were younger, he took them out on his paddleboards and windsurfing boards while he was at the helm. “That was the greatest thrill of my life,” he says.
For Massey and his circle, the water has long meant bonding—and so much more. “Of course you get to see the ospreys and the turtles and all the animals God makes, and that brings so much joy. For others, it’s all a way to have fun, get a workout and have some peace of mind. These sports are relaxing. It’s good for the mind and the soul to be on the water.”
One look at Massey’s face and it’s clear as the Gulf water that he buys what he sells. The man has a twinkle in his eye and an easy grin on his face. It’s no wonder that people want to know the secret behind the good life he lives.
Stop by his shop and he’ll readily tell you. Just don’t be surprised if you get hooked on what he says. Which just might be a good thing. After all, some may say the world doesn’t need more addicts, but if they’re of the Roy Massey variety, maybe that’s exactly what the world needs more of. Brooke Morton is a freelance writer specializing in the outdoors. She's also the founder of Sober Outside, a travel company for teetotaling adventure-lovers.
"TO KITESURF, YOU NEED AT LEAST 10 MPH, OTHERWISE YOU ARE JUST SWIMMING" ROY MASSEY