Windsurfing on Hilton Head: Then and Now


Hilton Head Island has been shaped by interesting people with equally interesting stories. Mike Overton, owner of Outside Hilton Head, is one of those people. His fierce love for the outdoors has and will continue to influence the way people experience and enjoy all that the Lowcountry has to offer. He’s already had an impact on the more than 10,000 people he has taught to windsurf.

“For the record, we were not the first to teach windsurfing. John Jamison was the first,” Overton said, as a slideshow of photos plays on a large flat-screen television in the conference room of his Shelter Cove store. Images of people I recognize appear and disappear in rhythmic time with Sailin' Shoes by Little Feat. I even see a photo of myself when I worked for Overton nearly 20 years ago.

Windsurfing2“Sailin’ Shoes Windsurfing was our original name when we started in 1979,” Overton said. “Back then, Windsurf was the only brand. There was one board and one design class. Charlie Fraser was our first fleet captain. We would have Wednesday night races and Reiner (Grengross) of Café Europa would put a keg out for us. By the mid ’80s, we were the largest windsurfing school in the country.”

Images are still scrolling on the screen and I catch glimpses of tanned bodies, unruly sun-bleached hair, and the beaches and creeks that formed my childhood — and are currently forming my children’s.

“Windsurfing somewhat peaked in the late ’80s,” Overton said. “The industry made a mistake by focusing on who was proficient in the sport versus entering for social reasons.”

And then John Brackett, a renaissance man to many, blew in. He changed how Overton and others caught wind on the water.

“I would wake up to the sound of his kite outside my door,” Overton said. “He would be on the beach flying stunt kites and, as soon as someone connected a stunt kite to a wakeboard, he was the first to master it.”

Kiteboarding took off in the early 1990s and continues to grow in popularity — even former President Barrack Obama recently gave it a go. 

Whether you kiteboard or windsurf, according to Overton, Hilton Head is a water sport enthusiast’s paradise.

“Hilton Head has good consistent wind year-round. It’s even better in the warmer months because of thermals, with May to June being the best time,” Overton said. “We also have beautiful wide beaches so it’s easy to launch.”

As for what draws people to both windsurfing and kiteboarding, Overton says that no other sports connect you with so much natural power. “With sailing, you are driving. With windsurfing or kiting, you are actually part of the rigging and completely connected to wind and water. It’s pretty exhilarating.”

When it comes to the two sports, “you can divide them by hair color,” Overton jokes. “All the gray-haired people on the beach are still windsurfing.” But what unites both sports are the people that enjoy harnessing the wind. “We’re a tight-knit community.”


  • BOARD AND RIGGING Basic equipment like board and rigging (mast, boom and sail for windsurfing; kite and bar set for kiteboarding)
  • INSTRUCTION Overton recommends an immersion course like REAL Watersports in Cape Hatteras, North Carolina
  • WET SUIT for colder months; BATHING SUIT for warmer months
  • RASH GUARD OR MICROFIBER SUN-PROOF SHIRT(available at Outside Hilton Head)
  • WATERPROOF SPORTS SUNSCREEN like Watermans SPF 50+ Aqua Armor Lotion (Men’s Journal recently named it “the most water-resistant sunscreen”)

Becca Edwards is a wellness professional, freelance writer, and owner of b.e.WELL+b.e.CREATIVE (