Joe Keenan, center, performing at the memorial service on Friday.
Jeanna Shepard

Still Sailing With Captain Bob

If you had been sitting on the beach in Menemsha preparing to watch the sunset this past Saturday you witnessed a rare thing.

If you had been sitting on the beach in Menemsha preparing to watch the sunset this past Saturday you witnessed a rare thing. You might have thought that there as some sort of invasion taking place. You may have thought that time had shifted and you were transported to another planet and were being invaded by a strange cadre of ships from a time long ago. Flying ships of a sort, yes, because they did have wings that stretched from the sea up into the air.

One of these conveyances was larger than the rest, perhaps the mother ship you might think to yourself because it seemed the other smaller vessels stayed close to her and when she turned into the wind and set anchor to the sea floor the others slowly in turn followed suit.

If you were close enough you could see names painted on them, names from different places, some you might recognize and some you might not: Malabar, Phra Luang, Macnab, among others, and on the mother ship, Shenandoah. And nearby, perhaps her sister ship, Alabama.

The sight from shore of these vessels as they arrived like clouds of white moving in synchronicity might seem strange but certainly a wonder. Ot might make you feel like the timeline you had arrived in was the distant past even though in fact you were right here right now.

In was in fact a collection of some of the finest sailing vessels from Vineyard Haven and in fact some of the finest of the world. There was a reason why they now had gathered together, why they had all left Vineyard Haven that morning to be joined by other ships from far away to sail up the Sound and as a magnificent flotilla turn up into the wind and let go their anchors just off Menemsha Beach.

That reason was to pay tribute to a man all of those aboard all of the vessels had known and loved. A man who had brought many of them into the world of sail. A man who was perhaps most responsible for making Vineyard Haven a mecca for wooden boats. This was the finest way they knew to honor the life of Capt. Robert S. Douglas, who many had simply called ‘Bob’.

On board the Shenandoah for that sail you would have encountered former crew members, first mates, Bosun’s and cooks, even a chanty man, who all lovingly served time aboard in years past. But they weren’t just there to spin yarns, as all sailors do, they were there to sail and as they did you you would have heard them speak in the strange language of sailors.

“Take up on the jib!, ready on the braces! All hands to the main halyards port and starboard! Peak and throat!”

And finally when they arrived, “Drop the hook!”

That’s when the yarns commenced in earnest. Notably, there were two who had been on the maiden voyage in 1964 from Maine to The Vineyard: Tony Higgins and Gerry Goodale. On the Alabama the make-up of the crew was the same: old salts and fresh sailors, Captain Bob’s sons, the list is long. Nearby on The Macnab was Bob’s much loved wife Charlene who had been at the helm all day, herself a seasoned sailor.

The thing is it wasn’t a distant time or place, it wasn’t some movie romanticizing the days of sail. It was in fact the here and now, a present moment that Bob’s life engenderd and fostered with love and dedication. And all on board all the vessels that day were there to share their love and admiration for whom they all mostly called, The Captain. In the best way they knew how.

In the morning on Sunday the question arose as it does when beginning any journey on a sailing ship: “Will the wind and tides be if our favor?”

At first light it was still in question but shortly there after the mate called out, “hands to the windlass!”

And somehow it seemed wherever The Captain was now residing after his passing this past spring, he heard the clank, clank, clank of the windless, and the flaking of the chain on deck and his spirit awoke. It must be so, the wind came up in the perfect quarter, the tide was fully fair and would remain so for hours.

And the call came again from the mate: “All hands to the Main! Heave away!”

All the others followed in kind and once again like in the days of old the fleet of white clouds sailed for home, down the Sound to Holmes Hole. Once again we were all sailing with Captain Bob.

Joe Keenan lives in West Tisbury. 

Comments

Submitted by Anonymous (not verified) on Tue, 09/23/2025 - 22:08

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Helen Koch Vineyard Haven

Thanks Joe for singing for my friend Noreen Baker. She would have loved to been at Capt Douglas tribute. She’s now in the sea with all those lovely boats. Missing her lots. ❤️

Submitted by Anonymous (not verified) on Wed, 09/24/2025 - 16:03

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Roy Vella Boston

Beautiful tribute, Joe, as were all your songs throughout the weekend. Could not have imagined a more perfect memorial for the Captain... calm winds and waters for the Friday evening program, allowing both ships to be docked creating a somewhat "cozy" environment with the hulls making impromptu walls around us. And then absolutely blowing with blue skies on both Saturday and Sunday! Incredible. Maybe Cap had a hand in it.

Most importantly, the realization that we are all part of an extended crew that Cap built over decades. Crew mates over time and generations coming together to honor a great man. So glad that I didn't miss it and thank you, Joe, for this and all your parts in the experience.

Proud deckhand, 1990

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