Gary Maynard speaking at the memorial service on Sept. 19 for Capt. Robert Douglas.
Jeanna Shepard

Saying Goodbye as the Captain Steers a New Course

At 12:37 a.m. on Wednesday, April 23 of this year, Martha’s Vineyard lost an irreplaceable elder and we gather here today to grieve this loss together.

Editors note: The following eulogy was delivered by Gary Maynard at the celebration of life service on Friday for Capt. Robert Douglas.

At 12:37 a.m. on Wednesday, April 23 of this year, Martha’s Vineyard lost an irreplaceable elder and we gather here today to grieve this loss together. Robert S. Douglas was a truly remarkable man, a great man, a man who, by being true to himself and living his own unique dream, touched the lives of literally thousands of young people, and who profoundly influenced our community in ways we see all around us today.

Thanks to his vision and strength of character we have a vibrant waterfront that is different from any other in the world. We have these beautiful big schooners, we have an active wooden boatyard, we have the largest fleet of wooden boats in the country. We have shipwrights and boatbuilders, riggers and sailmakers and spar-builders. We have yachtsmen who have explored the far reaches of the world. We have merchant captains and mates and pilots who started their long maritime careers aboard his magnificent Shenandoah.

What we don’t have is marinas full of mass-produced sport-fishing boats and racing yachts. We do not have waterfront shopping malls. We do not have chain stores or high-rise hotels on our beach. Yes, Bob did not fight each of these battles himself, but it was his leadership, his example, starting in the early 1960’s, that set the stage for the unique community we have here today.

Few who met him were not struck by this unique and powerful man, his commanding physical presence, he penetrating gaze, his natural gravitas, his astounding memory for the smallest detail of the things that mattered to him and his uncanny sense of direction.

“Bluenose was built in Lunenburg at Smith & Rhuland, just down the beach east of the Dory Shop. The Foundry had railways much farther west, up to the head of the harbor,” he might say, having last been there in 1960.

I was there a year ago and couldn’t tell you north from south.

He had an encyclopedic passion for the arcane and the historic, and anyone in his presence would listen with attention. Okay, I admit, a good portion of those listeners would be just trying to figure out what the heck he was saying.

Bob Douglas was a masterful sailor and an unequaled keeper of the flame in the final seconds of the sunset of the Great Age of Sail. Shenandoah was the last square-rigged vessel to be built at a commercial wooden shipyard in America. Her masts were turned at Pigeon Hollow Spar, the last of the great spar-builders. Her blocks were made by Boston Lockport, block-maker to the great clipper ships. Her windlass and her coal stove were cast at Lunenburg Foundry, the last of the great maritime iron foundries and her iron-wire rigging seized and spliced at Bohndell’s loft, the last of the old-time ship riggers. She was built in the final moments before these historic resources were gone forever.

Her running lights are oil-fired, her meals cooked with coal, her cotton sails hoisted with Manila rope. Shenandoah is not a replica. She is, in the words of my friend Capt. Daniel D. Moreland: “The last great American sailing vessel.”

She is an irreplaceable artifact of tremendous value and is the oak backbone of our waterfront town.

However, the character of Vineyard Haven today and the enduring grace of Shenandoah underway in Vineyard Sound are not Bob Douglas’s most important legacy. It is the experience he gave thousands of schoolchildren and hundreds of the young men and women of his crew over more than a half-century in command of his historic vessel. To them, a week at a time, he gave a glimpse into the 19th-century past, a quieter time when the pace of life was dictated by wind and tide, each day one of a little hard work, of sun and a summer sou’wester, a day living in the moment in the company of shipmates, where the outside world recedes into a haze on the horizon astern. And at the close of each the day the belly is full of hearty food and a starry night watch begins or a warm bunk beckons.

My story is one of the many, many stories about Bob’s influence on a young man’s life. Harvey Gamage laid the keel of Shenandoah the year I was born, and Shenandoah has always been a presence in my life. I vividly remember her coming up Fisher’s Island Sound when I couldn’t have been more than eight years old — a vast, looming apparition of spars and canvas and gleaming white topsides. As she glided passed our little Key West smack, an imposing red-haired man leaned over the stern davits, watched for a few moments, and gave us a wave. Bob was always a sucker for a pretty boat.

I signed aboard Shenandoah at 16 years old, washed dishes, set tables, tended the coal stove, jumped through hoops for the cook and set about learning the lines, the commands, the maneuvers, the routines and the culture that would allow me to rise through the ranks, from galley boy to deckhand to bosun and to mate. I learned to line up the cut cobalt glasses when setting the 18-foot mahogany tables, to black the stove, to clean the skylight so the mate couldn’t wipe a finger around the lip and find coal dust.

I learned to chamois varnish, polish brass, to jump for a bucket and sponge should a footprint appear on the paintwork. I learned to roll a topsail bunt so tight it couldn’t be seen from the deck, to haul a brace with everything I could muster, to race aloft to handle sail, to pilot a yawl boat under the stern in a chop. I learned to sand and caulk and paint with no curtains, no holidays and no splatter. I learned to herringbone a torn headsail, to trim a lamp wick to perfection.

There were no lessons, no program, no instruction, no praise, only the highest of expectations. We sailed on and off the hook, spreading all canvas in minutes, everything on the double. Later in the day, we would roar into a familiar harbor all sail set, only to round-to and swiftly douse sail without a hitch, and we would flake her great white wings for the night, the miter seams running precisely up the center of the stowed headsails where they sat high and tight on the top of the jib boom.

I became part of the tapestry being woven by the forbidding, quiet man with the flaming sideburns who stood all day, every day, year after year, back at the wheel. Through force of will and strength of character Bob Douglas maintained those threads of knowledge passed down from generation to generation since man first put to sea, those standards, those hard-earned rites of passage that made his working vessel so dynamic, so real and so important.

My wife Kristi and I met and were married aboard Shenandoah. Kristi was herself once a Sunday bunk-maker on the schooner (ask her about the required 10 inches of turndown and, yes, Bob always carried a tape measure). We bought our own Violet from Bob and re-built her in his shop at Five Corners. We rented our first home from him over the Coastwise Packet Company shop. We rebuilt Charlene’s lovely MacNab and worked together for another 15 years culminating in our collaboration resurrecting the Alabama. In these efforts, and indeed in all things, we strived for the integrity and the excellence that we learned aboard Shenandoah.

Through it all, Bob and Charlene welcomed us and our children into their lives. Bob was first my captain, then a mentor and collaborator and then for decades my friend. We shared a passion for traditional architecture and construction, for old trucks, for sailing ship design that I rarely found elsewhere. We always had something to talk about, right up until his last days. He eyes would light up when he saw me, he’d shake my hand, and as he got older, he’d thank me for coming to see him. On his 90th birthday I thanked him for allowing me to be a part it all, to be the Mate of a topsail schooner in the 20th century, how lucky I felt to have sailed and lived and loved Shenandoah in the tradition of the great tea clippers. I told him she was still

my favorite vessel of all. His eyes sparkled, he beamed and he gave me a bear hug. In 40 years, I had never told him this and we had never hugged.

I sat at the foot of his hospital bed in March, watching him as he slept. When he woke, he asked accusingly: “How long have you been here? You should have woken me up.”

And then he showed me the lines of the topsail schooner Vaquero he’d become interested in and we dissected it with his usual insight until he fell asleep again.

The last two months of his life Kristi and I visited Bob almost every day and we will be forever grateful for the love we were shown by Charlene and the boys, welcoming us into this most intimate of times. It was a profound experience to be there, embraced by Bob’s beloved family, allowed to comfort and to be comforted as he reluctantly prepared for his last voyage. Charlene was amazingly strong, hopeful and tender as the love of her life slowly slipped away. Robbie, Jamie, Morgan and Brooke were patient and kind and incredibly attentive to their father. We called ourselves the Night Watch and for seven weeks one of us was always at his side, whether by the fire chatting, sitting next to him on the couch as he dozed or at his bedside, his four dogs splayed out on the covers next to him, standing a vigil of their own.

When he could no longer speak, he would listen with those deep, bright, penetrating eyes wide open, and we all made solemn promises to keep one part or another of his legacy alive. Even in his final days he had a magnetic force of will, persuading each of us to reach for something of value, to hold on to our history, to carry the torch of tradition into the future.

My friend Bob Douglas has now crossed Vineyard Sound for the final time. Eight bells have rung and our old shipmate’s last watch on this watery Earth has ended. I struggle to find a new balance in a world knowing he is not down at his shop, or reefing a troublesome deck-seam on MacNab, or in his rocking chair by the fire at Arrowhead. Perhaps he is enjoying a brisk sou’wester, broad-reaching across a sound not so far from here, resolutely steering a course toward a cove he likes. He won’t need to read a compass to know which way is north, that I’m sure of.

Goodbye, Bob and Godspeed, Captain.

Gary Maynard lives in West Tisbury. He is a founding partner of Holmes Hole Builders, LLC.

Comments

Submitted by Anonymous (not verified) on Mon, 09/29/2025 - 18:45

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Jill Melody North Queensland, Australia

Oh Gary ~ what a beautiful eulogy.
There are tears in my eyes as I comment on your amazing stories about this very special man. Sending love to you all. Wish we were closer.
Thank you.

Submitted by Anonymous (not verified) on Mon, 09/29/2025 - 18:48

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Sally Presbrey New Bedford

I spent my summers in Padanaram my parents had their summer home right on the water. Tuesday or Thursday the Shenandoah would sail in and anchor right out in front . How very lucky we were . RIP Capt Douglas

Submitted by Anonymous (not verified) on Mon, 09/29/2025 - 19:59

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Luke Melody The Antipodes

Well said Gary. Bob Dougals’s magnetic personality attracted a great group of traditional sailors to Coastwise Wharf and his cement shed who will agree with everything you have said and carry his vision to a new generation. I feel certain this will be the way honour his life, and all he would have hoped for.

Submitted by Anonymous (not verified) on Mon, 09/29/2025 - 21:14

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Edward Jordan St. Croix, US Virgin Islands

Truly lovely!

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