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.
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.