It's said that her name is Indian by origin and means Daughter of the Stars, but in truth she is more like the daughter of Capt. Robert S. Douglas. He planned for her, he provided everything she ever needed, and in return, she has never gone anywhere without him.


Captain Douglas first sailed the Shenandoah, a 108-foot topsail schooner, into Vineyard Haven harbor in 1964, after overseeing her construction at the Harvey F. Gamage Ship Building Co. in Maine.

Her hull is made of native Maine oak. Her decking and ceiling are pine. Her masts are made of West Coast fir and weigh two and a half tons each. She measures 152 feet long overall, 23 feet wide and draws 11 feet.

And she has no engine.

That makes her the only square-rigged vessel in America operating without power. Traveling within the reins of the winds, currents and tides, this is the Shenandoah's 44th summer sailing Vineyard waters, with Captain Douglas at her helm.

That makes it surprising to recall that the relationship came close to ending 20 years ago.

In 1987, Captain Douglas put his daughter of the stars up for sale. He planned to retire as her captain at 55 years of age - and he already had plans to build another schooner. At that time, The Black Dog Tavern had been open for more than 15 years and the creation of the Black Dog T-shirt roughly seven years prior was about to turn the company into a multi-million dollar retail empire. As Captain Douglas recalls, "The tail started wagging the dog. It started as a restaurant and it turned into a dry goods business."


But on a recent summer afternoon, sitting in his attic-like office overlooking the harbor, filled with books, boat models, photos, artwork and myriad nautical items, Captain Douglas, now 75, said little about what led him to keep the Shenandoah and remain her dedicated captain. In his characteristic way, given to gruff mumbling and short answers until a topic interests him and his eyes begin to twinkle and he begins telling tales. He recalled simply that all the people who wanted to buy her were, in his own word, "wackos."

Keeping her suited him fine.

Twenty years after the fact, he spends his days much the same way he did then - on the Shenandoah.

"I don't get that involved with the food or the clothing," he said. "I think we have 14 stores. I'm not sure. I should know."

His four sons have all grown up, and each has chosen to play a part in the family business. Robert Jr., 36, is chief operating officer of the company - no longer called Coastwise Packet Co. & Wharf, but The Black Dog Tall Ships and The Black Dog Wharf. James, 34, manages the retail stores. Morgan, 30, skippers the 90-foot schooner Alabama, and Brooke, 25, skippers the Black Dog's newest schooner, Chantey. At one point, all six family members - including Captain Douglas's wife Charlene - had their captain's licenses.

"I almost lost Jamie and Robbie to the windsurfing game, but they sort of came back to the fold, as it were," Captain Douglas said. "Every time it's blowing over 30 knots, there's a sign on the door that says ‘Gone windsurfing,' "

Everyone in the family except for Captain Douglas windsurfs - including his wife.


"How they don't all get killed, I don't know," he quipped. But Captain Douglas is obviously pleased with his family, and the fact they all live on the Island.

"I'd say it's very unusual. Most families are spread out all over the country," he said. But he doesn't care to contemplate whether it's common interests or family values or any particular brand of child rearing that led to that. "They must like it here," he said simply.

Captain Douglas loved the Island from the time he first rented a house with his father in the summer of 1947. He was 15.

"It used to keep me going through school thinking I'd be back here next summer," he said. He remembers wishing he could be among the people on the ferry dock who would wave good bye to him at the end of the summer. At 26, he moved to the Island year round.

Shenandoah's next turning point came in the early 1990s, when the charter business hit a slump. The cost of plane tickets plummeted, making a flight and stay in London less expensive than a week on the windjammer. The solution was found on Arrowhead Farm, the West Tisbury horse farm on Indian Hill that the Douglases have lived on and run since 1983. He recruited the children in the riding program to come aboard the Shenandoah.

"We infiltrated the school system from the back door," Captain Douglas said. "We've been carrying five schools of kids ever since."

This is the 13th summer the Shenandoah has taken groups of up to 29 young people - aged nine to 14 - on voyages of a week or more. This wasn't the first time kids were taken aboard though. Mariner scouts from Illinois were among the first passengers in the 1960s. The mariner scouts, a branch of the Girl Scouts, became a fixture on the Shenandoah.


In the summer of 1970, Captain Douglas met a mariner scout leader named Charlene LaPointe and married her.

"I wish I'd come into this kid option earlier, because it's a win-win situation," Captain Douglas said. "We've been stuck in fog three days and the kids still have a good time."

Many adults would have stopped payment on their checks by then, he said.

"They want to know where they're going to be and when they're going to get there," he said of grown ups. "As human beings age, they tend to lose their resiliency."

Thirty years later, he still remembers the passengers who were impossible.

"I brought up four young men myself and if I had to pick what age they're the best, I'd say 11," he said. "I need a bright eye and bushy tail, and most 11-year-olds have that."

They're sponges for information, he said, and with a group of them, there is plenty of manpower to hoist the sails and haul up the anchor.

"It's the best size and age of kids - of people, I should say."

By his rough calculation, over 5,000 young people have had the Shenandoah sailing experience.

"It's not a hard and fast curriculum like a school. The vessel's lifestyle creates the curriculum," he explained. Even in fog, there are things to do: swimming over the side, learning to tie knots, handling lines.


"I most likely get some kind of vicarious satisfaction in providing an experience that wasn't around when I was a kid," he said. "An important product is carrying passengers - to give that experience to the kids. There's no boat like Shenandoah." Not having an engine aboard the vessel makes it "a whole different involvement," he said.

On both the Shenandoah and the Alabama, there is one mate, one bosun and five or six deckhands, meaning that all told, about 500 young people have also had the opportunity to crew on one of his tall ships. Most mates and bosuns worked their way up the ranks.

"I've only hired three mates outside the club, so to speak," he said. For example, the Shenandoah's current mate started as a deckhand at 15, then became bosun and at 18, became mate.

Captain Douglas has no doubt played a role in keeping sailing - especially, historic 19th century sailing - alive.

"We're in unusually good shape here. I think we have 10 or 12 schooners right here in the harbor," he said. With sailmakers, boat builders, marine stores and crew, "we've got the whole nine yards here, which is pretty unusual."


Five topsail schooners have been built in the United States since he designed and built the Shenandoah based on an original 1850 design of the fast revenue cutter Joe Lane.

"The best thing, in retrospect is to look back and see this industry is not dying away, because you've got to have new construction," he said.

Even the hard labor on a wooden boat is rewarding, Captain Douglas said.

"You get out exactly what you put in," he explained. "If you can get someone involved with having to caulk and having to sand - just the maintenance of a wooden boat puts you in a relationship with the boat. I know every inch of my schooner. Most people don't get involved that way."

Twenty years after he might have given her up, Robert Douglas has no plans to retire as captain of the Shenandoah.

"I just got infected a long time ago, and it stuck with me," he said. "I've been on vacation all my life."

Picturesby Alison Shaw