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Bob Douglas

Sea Captain + Brand Guru  \\  Helping keep Vineyard Haven timeless

There is something completely unique about entering Vineyard Haven. The harbor, despite the season, possesses a timeless quality as though any era from the last 400 years can easily be imagined. Captain Bob Douglas, founder of The Black Dog and the Coastwise Packet Company has been a major influence for over 50 years in the lore, mystique and romance that makes Vineyard Haven so special. Douglas, who always refers to anything within The Black Dog Company as a “she,” just as any captain worth his salt would of any enterprise under his commission, was at the helm from the beginning. What began as a tavern, and continued with the launch of a t-shirt in 1981, The Black Dog has become one of the world’s most recognizable brands. The beginning though was simple and humble, like Douglas himself. “She opened for business the first day of ’71,” Douglas explains. “Vineyard Haven didn’t have a good year-round restaurant.” A friend who was a local carpenter, a waterfront piece of property on Vineyard Haven harbor, and a pile of recently acquired 18-foot heart pine beams were all the ingredients he needed to create the infamous restaurant that started it all. Named after his favorite dog, a friendly, mostly black female named Black Dog, the rest certainly has become history.

Ironically, history is where Douglas is most comfortable. The other half of his enterprises falls under the command of the Coastwise Packet Company where his iconic Black Dog Tall Ships have also become part of the collective conscience of Martha’s Vineyard. Shenandoah, a square-topsail schooner, and Alabama, a former Alabama bar pilot boat that was re-fit as a schooner, are Douglas’ passion projects. “Like most things, when you are involved with other people who are in similar enterprises, things have a way of happening,” he recalls. “I had the good fortune of spending a summer working for a gentleman named Ben Hawkins who had two schooners in Sedgwick, Maine. I also spent part of a winter as a deckhand on the boat that was used in the 1962 “Mutiny on the Bounty” movie with Marlon Brando. When I returned from delivering that boat to Fiji, I had an opportunity to work with Hawkins again. I ultimately stepped up and put down my deposit, and in February of ’64, Shenandoah was launched. That’s what has been keeping me out of trouble ever since.”

“Last year was my 55th season with the same boat which is really unusual. She has conditioned my whole life since 1964. She is my major commitment. It is a full six month operation from fitting her out, to running her, to laying her up,” Douglas explains. “You can work all winter long maintaining everything.”

The Alabama found its way to Vineyard Haven harbor in 1967 when Douglas brought her up from Florida. “She sat as a fixture in the harbor for almost 30 years until our ducks lined up in a neat row,” Douglas remembers. “She was never fit with a sailing rig when she was working for the Alabama Pilots in Mobile, but we took care of that.” Sure enough, over three years and replacing over 90 percent of her original form, Douglas and his crew were able to bring the dignity of a nineteenth century fishing schooner to her humble service as the second ship in the Black Dog fleet.  

These historically emblematic vessels set the stage for the sentimentality that permeates the harborfront. Stepping foot into the small, old-world space that serves as Douglas’ operations offices on Coastwise Wharf is like looking down the shaft of a spyglass into another era. “I’ve got a pretty good collection of nautical junk,” Douglas says wryly. In fact, it is an enviable assortment of finely crafted, half-hull models chronicling the history of competitive sailing, dozens of framed photographs of boats exposing impressive keels as they are healed over, finely carved quarterboards, antique charts depicting exotic harbors, navigational tools of an age gone by, and generally cool stuff for anyone who, in the words of Rudyard Kipling, enjoys, “simply messing about in boats.” 

The next generation of Douglases includes four sons who have stepped aboard to keep things sailing smoothly. Each is different in his own right, yet they all share their old man’s simple love of the sea, and their progeny seem destined to carry on as well. “They got their kids all swimming in the water, under the surface of the pool at the Mansion House here in Vineyard Haven, and they aren’t four years old yet,” Douglas confirms.

Douglas’ ability to focus and recognize the rare value of the past is unique because it bears upon his ability to chart and navigate his future. When asked what is next for The Black Dog, Douglas chuckles and says, “I can’t expect to be doing this forever. Right now, I keep an eye to the weather and see what the next step is.”

For more, visit theblackdog.com and theblackdogtallships.com for more!

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