This week concludes Capt. Robert Douglas’ 50th summer skippering the Shenandoah, what amounts to the longest-running relationship between a captain and his boat he’s ever heard of.

“To my knowledge, no one has ever been tied up to the same boat, without interruption for 50 years,” he said this week on the porch outside his office in Vineyard Haven.

Shenandoah, the 108-foot square topsail, modeled after a mid-19th century schooner, predates Captain Douglas’ other ventures, the Black Dog restaurants and the multi-million dollar company founded on the silhouette of his pet dog, which now counts 22 retail stores nationwide. The real black dog passed away decades ago, though she’s immortalized on T-shirts that outsell any other in the United States except for the Hard Rock Cafe, Mr. Douglas said. 

Though they are unquestionably adorable, the Jack Russell terriers, Snoopy and Fluffy, that gaze lovingly at Mr. Douglas will likely not enjoy the same fame. Tethered to their owner by some nautical-looking rope, the two sniffed around the porch and inspected those who crossed the threshold into the Black Dog Tall Ships lobby. But mostly they were content to sit and listen to Mr. Douglas tell his tale. 

Mr. Douglas, now 81, wore boat shoes, a light green polo with a discreet black dog silhouette printed on its sleeve, and a weathered 2012 Shenandoah cap with two pins stuck in it bearing images of the boats that make up the company’s fleet — the 90-foot schooner Alabama and the Shenandoah.

Until three weeks ago, Mr. Douglas was the only person who had ever skippered the Shenandoah. His third son, Morgan, took the helm this month for a few trial runs. 

When he finally gets around to write his own book about his half-century relationship with Shenandoah, he will likely begin it with a photograph of his first ride in a little wooden row boat in Northern Michigan, where he attended camp at age six.

“That started it,” he said resolutely, referring to a lifelong passion for boating.

Mr. Douglas grew up in Chicago and came to the Island for the first time with his father in 1947. They rented a house, and Mr. Douglas focused his attention on the boats of the Island’s harbors.

“It started an exposure to boats I had never had at all,” he recalled.

Over the years, he owned several non-auxiliary boats, including a Vineyard Haven 15, a racing sailboat that he shared with his brother. The boat was 21 feet long, and built at the Martha’s Vineyard Shipyard.

One boat led to another and soon he was hanging around a Maine boatbuilder named Havilah S. Hawkins, who was building a coasting schooner for an Islander named Zebulon (Zeb) Tilton. At the time, historic coasting schooners were predominately used as cruise ships.

“The only real economic base for sailing schooners like that,” Mr. Douglas said, was touring the coastline with ticket-carrying passengers. In 1960 he was hired as a deck hand on the Stephen Taber, his first experience working on a historic, wind-powered schooner.

When Mr. Douglas speaks about the boats that inspired Shenandoah, his usually fast, quiet speaking voice slows down and grows louder. By the time Mr. Douglas decided to design his own boat, he had become familiar with a boatbuilder in South Bristol, Maine named Harvey Gamage.

Looking back, Mr. Douglas marvels at the chain of events that led him to Shenandoah. It’s almost as if each were part of a predetermined pattern. “It was all planned somewhere, it seems that way,” he said. “The planets and the stars were all in alignment.”

For five days the schooner’s contract literally hung over him in the driver’s side visor as he drove his Chevy station wagon around the Island. He mulled over what would be one of the most important decisions in his life — whether or not to finance the building of the mid-19th century replica for $170,000.

When he finally built up the courage

to drop the contract in a mailbox on Church street in Vineyard Haven, he knew he was locked into a long-term relationship.

“I’m setting up a continuum I can’t have any control over,” he said recalling that day. “I can’t get off. I am now on the boat.”

For a year and three months, not a day passed when Shenandoah wasn’t under rigorous construction at the Harvey Gamage shipyard. Mr. Douglas should know. He monitored the entire process, from the initial designs to the final rigging.

Shenandoah’s hull was carved from oak, her decking and ceiling are pine, and her masts are made of fir. At the end, she measured 152 feet in length.

On the day of the launch, Feb. 15, 1964, a northwest wind blew at 15 or 20 knots. At his friend’s suggestion, Mr. Douglas hired a bagpipe band from Lawrence to play celebratory tunes. The musicians’ knees stuck out of their kilts, red and raw from the dry cold. Hundreds of people watched as Mr. Douglas’ father christened the boat with a bottle of champagne. Shenandoah was named for a favorite sea shanty of Mr. Douglas. The name is Native American and means “daughter of the stars.”

Over the years, Mr. Douglas has chartered tours aboard the Shenandoah for Vineyard tourists and locals, and, more recently, Island schoolchildren. She has long stood as a defining feature of the Vineyard Haven harbor, instantly recognizable by her stately pair of masts and Black Dog flag.

In 1986 Mr. Douglas considered selling his boat. He thought he might invest in a newer and better boat. But the prospective buyers all asked the same question, could they install an engine?

While this is entirely possible, it would require an almost complete overhaul of the boat’s architecture. In the end, she “wasn’t very salable,” he said.

As this summer winds down, and her 14-week season comes to a close, Shenandoah’s future is undetermined. Mr. Douglas is noncommittal about whether he will continue to be her captain or whether Morgan will take the lead. “I don’t know what is going to happen next summer,” he said.

While Shenandoah was built for $170,000, Mr. Douglas estimates that she would cost five to seven million dollars to replicate in today’s shipbuilding market.

Shenandoah is designed for speed. She’s better suited to carry passengers than cargo, and not just any type of passenger. A trip on the boat is hard work. The passengers must help out with almost every one of the boat’s locomotive and maintenance responsibilities, as the modest crew of nine cannot handle it on their own.

School-age kids have made up 99 per cent of the passenger load for 15 years, a fact that makes Mr. Douglas particularly proud.

“I wish I had specialized in kids before I did because they are the real way to do this,” he said. “It produces a win-win situation.”

For 15 years Shenandoah has hosted the Island’s youth on overnight trips lasting up to six days, mostly for fifth graders, a group Mr. Douglas finds particularly suited to the Shenandoah lifestyle.

“I would strongly approve of bonsai-ing people right around 11,” he said. “Eleven is the perfect age.”

When students set foot on his boat for the first time, they are in awe. “They are just great big sponges, they can’t get enough,” he said. “Everything is new and interesting. I provide the platform, a different lifestyle, one that is entirely different from anything they have ever experienced.”

While on board, the kids are assigned to a schedule of galley duty, and are subject to room inspections once or twice a day, depending on their cabin’s cleanliness. While the adults who voyage with him are often more than perturbed by a three-day fog event, kids couldn’t care less. “Grownups tend to lose their resiliency,” Mr. Douglas said. “That is the major grown-up problem.”

In periods of downtime, kids often jump from the boat into the water.

“Sometimes I think S/V [sailing vessel] should be changed to S/P: Swimming Platform,” he said. “They get a hell of a kick out of jumping off and swimming.” When the wind’s up, the students jump in to help hoist the sails and pull up the anchors. “I can’t sail the boat without the passengers,“ he said.

Over the half-century that Shenandoah has belonged to the Douglas family and the Island, she has carried more than 5,000 children and kickstarted the seafaring careers of more than 400 young adults who have worked as deck hands and mates. While he hasn’t gotten rich off the boat, he’s inspired a love of hard work and the sea in many young people.

“That justifies it for me,” he said.

For more photos of the sail, visit the gallery Sail on the Shenandoah.