Skip to content

Subscribe  |  Login  |  Account

The Quickest Windjammer

Before the mast with Martha’s Vineyard’s famous kiteboarder, Rob Douglas

kiteboarder, Rob Douglas

Douglas, a seasoned kiteboarder, turned his childhood passion for sailing into a more exciting hobby. Photo by Craig Kolesky

Ask Rob Douglas, a lifelong Vineyard Haven resident who is called by some the fastest sailor alive, if kiteboarding is a form of sailing, and he’ll hedge his answer. It’s sailing in the sense that your “boat” floats and the wind is your power source. But, says Douglas, it’s not traditional sailing in the sense of the two-masted schooners that his father, Robert Douglas, owns and loves. While the younger Douglas grew up on wooden boats, his passion is speed sailing, a subset of kiteboarding that requires high-level skills, innovative thinking and supreme self-confidence—acumen and attributes that he honed over 40 years of sailing, mostly on the New England waters that he proudly calls home.

Douglas’ love affair with the sea began when he was 16 days old—an age his father deemed appropriate to introduce his son to sailing and the family business. In addition to owning The Black Dog Tavern, Robert owns two schooners, the Shenandoah and the Alabama, which he operates as Windjammers out of Vineyard Haven Harbor. Like the archetypical story of so many fathers, sons, and boats, Rob shared his dad’s passion for sailing—he just needed to define his own style.

kiteboarder, Rob Douglas

Kiteboarders use the wind to propel themselves at top speeds across the water. Photo by Adrien Freville

This journey began in 1987 when he discovered windsurfing. “It was the most amazing thing I had ever done,” recalls Douglas. “I loved its simplicity versus sailing on a huge wooden schooner.” A lengthy and competitive windsurfing career began, but, as his skills increased, he realized that the number of “perfect” days (read: howling wind conditions) on the Vineyard were frustratingly rare. Given that he describes himself using adjectives including “impatient, hyper, and competitive,” he eventually became disenchanted.

In 2002, Douglas bought a kiteboarding rig, but his self-instruction didn’t take. Then, in 2005, he took a lesson, and his worldview evolved. “Kiteboarding allowed me to experience a more radical part of sailing with less wind,” he says.
One of Douglas’ biggest regrets about his windsurfing career is that the timing was always slightly off between his personal/professional life and his windsurfing ambitions. With kiteboarding, however, Douglas saw a new start; what he didn’t realize, however, was that the timing was perfect.

The path to holding the world record started when Douglas and his friend, Mike Gebhardt, began scouring kiteboarding magazines for an unchallenged niche. Douglas wisely recognized that while freestyle kiting was out due to his age (40), speed sailing looked approachable. At their first event in Spain in July of 2008, Douglas unexpectedly placed second; he and Gebhardt also received an invitation to compete at the Luderitz Speed Challenge in southern Africa that fall. The temptation to sail against the world’s fastest was irresistible and the friends mentally began preparing for “the trench.”

kiteboarder, Rob Douglas

Top kiteboarding athletes are invited to compete at the Luderitz Speed Challenge, held yearly in South Africa when winds are at their top speeds. Photo by Craig Kolesky

Speed sailing’s première event takes place each fall near the small diamond-mine town of Luderitz in the Republic of Namibia in southern Africa. Between August and March, strong winds howl from the ideal direction, drawing international crowds. Speed runs take place on the “trench,” a skinny finger of water that’s 2,297 feet long (700 meters), nine to 12 feet wide, and only one-and-a-half feet deep. At one end is a pre-start phase where kiters gather speed before entering their run; on the far side is the slow-down phase. In between is the precisely measured, 1,644-foot (501 meters) official run. Speeds are calculated and averaged over this official run using computer-controlled cameras. The fastest certified speed fetches the podium’s top step, and representatives from the World Speed Sailing Record Council—the official governor of speed-sailing records—are on hand to witness any new world records.

Amazingly, Douglas quickly established a new outright world record of 49.84 knots, becoming the first kiteboarder to hold this title (the previous owner was a windsurfer.) The record didn’t stand for long, however, as a French rider named Alex Caizergues pulled a juggernaut and bested Douglas’ record by a mere 0.03 knots.

kiteboarder, Rob Douglas

Kiteboarding is quickly gaining popularity as the ideal water sport for thrill-seekers. Photo by Adrien Freville

Douglas returned home the fastest American afloat, but this wasn’t enough. He began testing new board designs and kite shapes, and he honed his fitness and flexibility. Ironically, history repeated itself at the 2009 Luderitz Speed Challenge when Douglas set a new world record of 50.95 knots; that same day Caizergues again out-sailed him by 0.03 knots. “Rob knows his skill set…[and] who’s in his class,” says Bill Lynch, Douglas’ close friend, sponsor, and fellow kiteboarder. “Alex is one of them. Each sets the standard for the other.”

In 2010 the stakes were raised. The “trench” was straightened to allow for faster runs, but at the expense of a proper slow-down phase. For Douglas, it was an opportunity to take back what was his, albeit with increased risk.

Douglas made history on October 28, 2010, during the Luderitz Speed Challenge with a blistering run of 55.65 knots, eclipsing the existing world record. Given the chance of an initial inaccurate reading, Douglas opted to take a second run to help consolidate his standings. While this didn’t yield a new record, it ended in infamy when he wrecked at 50-plus knots, breaking his wrist. “Crashing in the trench is serious,” reflects Douglas. “It’s fine if you bounce and skip, but you want to avoid coming to a full stop quickly.” Douglas reluctantly returned to Boston for orthopedic surgery, apprehensive about whether his record would stand. Fortunately, the surgery went well; even better was the news from Namibia: the world record was still his, despite serious challenges.

Back on the Vineyard, life resumes a comfortable rhythm. Douglas’s job as the CEO of The Black Dog Tavern allows him to work with one eye towards the sea—just like his father—and his evenings are enjoyed at home with his wife. For Douglas, this is a fine outcome to an even finer scenario. Given his fiercely competitive nature, he knows he’ll be prepared for Luderitz this fall. But, far more importantly, he also knows that he has already accomplished his goal. “To have grown up on the Vineyard, with a father who placed such a strong emphasis on sailing,” reflects Douglas, “to inject the Douglas name into sailing’s history, is a unique thing.”

David Schmidt is the editor of, editor-at-large at SAIL magazine, and is the owner of Alembic Media, LLC. He lives in Seattle, Washington.

You might also like: