‘My Shenandoah’

From inspiration to reality, Bob Douglas' story is told in a new book.


The Vineyard seems to attract characters on a mission of one sort or another, and no one exemplifies this better than Robert S. Douglas, whose imprint on Vineyard Haven Harbor, wooden boatbuilding, and sailing in general has been transfiguring. Not many folks who first come here on a ferry fail to notice one of the majestic schooners moored here, either Alabama or, more striking still, Shenandoah, both the brainchildren of Bob Douglas. And to those of us who have been here awhile, Shenandoah is so familiar that we’ve developed something close to a proprietary interest in her. When she’s not at her mooring, we notice.

As Doug Cabral tells us in the prologue to “My Shenandoah: The Story of Captain Robert S. Douglas and His Schooner,” the stamp left on those who have experienced Shenandoah firsthand is permanent. “Douglas’ unique and resolute vision [was] so compelling and so influential that most of those who have sailed in her, young and old, crew and guests, bear today the indelible mark of the matchless charms, the rigors, and the lessons learned aboard one man’s time-shifting creation.” Hyperbole? Not to me: I know Shenandoah alums who’d as soon use a fid as a toothpick to clean their teeth, others who still season their lexicon with marine jargon decades after coming ashore.

The second of four sons of a prominent lawyer and investment banker who lived in Lake Forest, Ill., Robert first came to the Vineyard in 1947 when his family rented a summer house on West Chop. He was 15. He’d been introduced to sailing as an 8-year-old at camp on Lake Michigan, but he was more interested in horses as a boy. The family’s first boat here was an 18-foot Menemsha-class sloop, Lucky, followed quickly by Wideawake, a Vineyard Haven 15, designed and built by Erford Burt, a local legend in wooden boatbuilding. Sailing was just one of his summer activities; flying came first. Trained by Carolyn Cullen on and off the grass runway at the old Oak Bluffs Airport, he first soloed in 1949, when he was 17.

After graduating from Northwestern in 1955, he spent three years in the Air Force ROTC, earning his wings in an F-86 jet fighter. He was encouraged to make a career of the Air Force, but, as he recalls telling his father, “I’ve tried the 20th century. Flying a jet aircraft is the most unnatural thing a human being can do … I want to get back to the waterfront.” And on the water.

His first oceangoing boat was Ayuthia, a 48-foot teak ketch that Douglas bought in 1958 and took south the next two winters. In 1960, looking through “History of American Sailing Ships” by Howard I. Chappelle, Douglas spotted the 1848 plans for a fast topsail schooner built for what became the Revenue Cutter Service, precursor of the Coast Guard. Modeled after the latest, fastest clipper ships of the time, the plans called for a distinctive rounded stern, low freeboard, and a rakish clipper bow. She was long, low, and sleek. The image fascinated him. By this time he was mate on the Stephen Taber, a former coastwise freight-schooner-turned-windjammer cruising the Maine coast.

His next berth was on the HMS Bounty II, a replica of the original that would star in the 1962 MGM movie “Mutiny on the Bounty,” on location in Tahiti. Much of what Douglas learned on the 7,000-mile trip from Nova Scotia to Tahiti was how not to rig and run a square-rigger.

Back in the Northern Hemisphere, Douglas’s plans for Shenandoah started to take shape and quicken. Her keel was laid on May 1, 1963, at Harvey Gamage’s shipyard in South Bristol, Maine. She was launched on Feb. 15, 1964, overbuilt in many respects — and gorgeous.

When Tony Higgins signed on as first mate soon after her launching, he was a knowledgeable, dedicated sailor — with zero experience aboard the likes of Shenandoah. “That first summer we were all learning how to sail a schooner, including Bob,” he told Cabral. “It was a whole lot of shaking down … In fact, the maiden voyage was absolutely hair-raising.”

Because of a long, excruciating duel with the Coast Guard to get Shenandoah certified to carry paying customers, Douglas took passengers for free the first summer, 1964. It was another year before he could charge customers, the fulfillment of a dream that could have only been effected by a tireless, devoted detail freak — like Bob Douglas. Now came the sailing and caring for her. Gary Maynard, a successful Vineyard home builder, was one among many impressed by Douglas’ fastidiousness. “It was the discipline … of keeping a clean vessel and caring,” he told Cabral. “And it’s a wonderful thing to be able, if you care, to do it all right. To be given the authority to do it right. And be given the expectation to do it right. The reward was the vessel. And that’s very 19th century,” when sailing was still a livelihood, and your life might depend on a knot tied correctly, the proper choice of sail.

Many other veteran crew members were interviewed and cited by Cabral, none of them about to forget their time aboard Shenandoah under Douglas. Matthew Stackpole, mate for several seasons, still marvels at Douglas’s “understanding [of] ship design and American maritime history, both schooners and other vessels. His knowledge is just encyclopedic.”

Then there are the aesthetics, in this case governed by Douglas’s eye. To him, a boat must be “knock-down, drag-out beautiful, she must sail like a witch, and she must steer like a dream.” All true of Shenandoah, thanks to Douglas’ inspiration made real, as Cabral puts it. The vessel’s impact has reached far beyond the people who have sailed on her, both crew and “walking freight,” as paying customers were once called. To Nat Benjamin, a mainstay himself of the local wooden boat community, “Douglas is a bigger-than-life figure … in the attention he has attracted to Vineyard Haven. Shenandoah is the flagship of Vineyard Haven, if not Martha’s Vineyard, grounding everything else that has happened here. The vessel is just a stunning example of what could be done in the 20th century.”

Though Douglas recently turned 90, he’s still looking forward. In 2020, he donated Shenandoah to the Foundation for Underway Experiential Learning, a nonprofit founded in 2016 by captains Ian Ridgeway and Casey Blum, both Shenandoah veterans. The plan is to maintain the old boat’s tradition of introducing young Islanders to the sea and sailing, while simultaneously raising money to build a larger successor. Made of steel, the new boat has been in the back of Douglas’s mind for 50 years, principally because of the headaches the Coast Guard gave him about licensing over the years. She will be larger than Shenandoah, and have auxiliary diesel engines, able to go South in winter so she can carry students year-round.

For readers who don’t know a gudgeon from a stanchion from a luncheon, a belaying pin from a bowling pin, there may be a surfeit of shipbuilding and sailing detail in these pages, but for anyone who has ever enjoyed messing about in boats (especially those made of wood), Cabral’s incisive account of the building and sailing of Shenandoah will be a joy. And the fine points take nothing from the story as a whole, compelling as it is, of one man following his passion by recreating the past to enhance the present.

Quick to acknowledge his longstanding friendship with Bob Douglas, it doesn’t hurt that Doug Cabral is an expert, both at the helm and at the desk. I’ve known both Bob and Doug, and been aware of Shenandoah, for more than 50 years, but this lively, pleasurable read offers fresh and fascinating tidbits about Bob and his boat, while paying tribute to his acute sense of purpose, dedication to detail, and willingness to take on convention. It is also a feel-good reminder of the author’s deep affection for, and knowledge of, boats and sailing, and everything else maritime, as well as his exceptional skill as a storyteller.

“My Shenandoah: The Story of Captain Robert S. Douglas and His Schooner,” by Douglas Cabral. Available at Edgartown Books and Bunch of Grapes. 



  1. Reading now, extremely interesting story. Captain Douglas, Shenandoah, Doug Cabral, island history. What more do you need.

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