Cruising Through History With Capt. Bob Douglas
Louisa Hufstader

A convivial crowd filled the Black Dog Tavern Wednesday night for the first in this season’s Sail Martha’s Vineyard dinner lectures. Capt. Bob Douglas was the man at the microphone.

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Embracing the Stormy Seas of Destiny
Joe Keenan

Growing up in western Massachusetts, I didn’t have much exposure to the sea, or to seafarers. It was by freak chance that I met my first sea captain.

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Shenandoah's Yawl Boat Destroyed in Harbor Collision

The U.S. Coast Guard investigated a mishap in which a fishing boat struck the yawl boat of the schooner Shenandoah Wednesday. The yawl boat, hanging from davits off the stern of the Black Dog ship, was destroyed; the two larger vessels were unharmed.

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Staying True to Shenandoah for 50 Years
Olivia Hull

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.

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Down to the Sea with Love: They come to the Island for a Memorable Voyage
John Budris and James D'Ambrosio

Down to the Sea with Love: They Come to the Island for a Memorable


For three magic days they were not heart transplant patients or the
leukemia kids in the next ward. They were neither stuck with needles,
nor looped through high-tech machines.

For three magic days their parents forgot about blood counts, organ
rejection and the next visit to yet another specialist at Boston
Children's Hospital.

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Captain Courageous: Robert S. Douglas and Shenandoah Remain as One
Rachel Nava Rohr

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.

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Topsail Schooner and Boatline Spar Over Town Harbor Space
Mike Seccombe

Since 1964, the tall ship Shenandoah has brought picturesque maritime charm to Vineyard Haven, moored in the same place in the harbor. But maybe not for much longer.

The Army Corps of Engineers has written to the owners of the 150-foot wooden sloop, the Douglas family, threatening to suspend the permit for the ship to moor there unless they can come up with some solution that resolves persistent complaints from the Steamship Authority that the Shenandoah is a hazard to ferry operations.

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Maine Shipyard Restores, Relaunches The Black Dog Tall Ship Shenandoah
James Kinsella

A thoroughly refurbished schooner Shenandoah was relaunched Saturday morning at Boothbay Harbor in Maine.

The Shenandoah, one of the Black Dog tall ships that sail from Vineyard Haven harbor, had undergone about six months of extensive rebuilding at the Boothbay Harbor Shipyard.

“We essentially did what is referred to as retopping — a rebuilding of the vessel from the waterline up,” said Bob Foster, a spokesman for the shipyard.

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Schooner High and Dry for Repairs — Again
Mark Alan Lovewell

Shenandoah, the graceful 108-foot topsail schooner that has long been a landmark in the Vineyard Haven harbor, is laid up at a Fairhaven shipyard, her majestic hull stripped bare and her ribs exposed as she undergoes extensive work to reverse a botched restoration job performed by a shipyard in Maine last year.

Robert Douglas, who is both captain and owner of the Shenandoah, has sued the Boothbay Harbor Shipyard for the apparently shoddy work that left his schooner taking on seawater last summer while she was filled with school children.

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Schooner Shenandoah to Move, Ending Long Dispute With SSA
Mike Seccombe

After more than a decade of wrangling which threatened to see the historic tall ship the Shenandoah removed from Vineyard Haven harbor, the ship’s owners and the Steamship Authority have reached an agreement which will allow the vessel to stay.

In deference to concerns held by SSA captains that the old ship presented a collision hazard to ferry operations, the owners, Black Dog Tall Ships, have agreed to move Shenandoah’s mooring within the harbor, to which it has added picturesque maritime charm since 1964.

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