My Shenandoah: The Story of Captain Robert S. Douglas and His Schooner By Douglas Cabral, Tilbury House Publishers, 2022, 163 pgs., $29.95

Douglas Cabral, at the beginning of his new book My Shenandoah, freely admits that although the book is in part a biography of legendary Vineyard sailing captain Robert Douglas, Mr. Cabral himself is not an unbiased biographer. He’s been friends with the subject of his book for decades.

“Some lucky folks serendipitously find themselves acquainted with and influenced by one or two unique people,” he writes. “Bob is one such for me.” 

At the heart of the story Mr. Cabral has to tell is a strange, in some ways inexplicable, spell cast over a young Midwestern man named Robert Douglas by Martha’s Vineyard, ships, and the call of wind in the sails. Mr. Cabral traces his friend’s adventures, from the Shenandoah’s maiden voyage in 1964 to the opening of Mr. Douglas’s mainland mainstay, the Black Dog Tavern in 1971, to Shenandoah’s time as a charter passenger vessel in the ensuing years. 

Readers get generous side-helpings of sea stories along the way. Over the years, the Shenandoah has seen many guests and hands and mates, and Mr. Cabral has talked to enough of them to fill a book twice this size with anecdotes about everything from nasty squalls springing up out of nowhere in the Rhode Island Sound to “the dog that started it all” (a dog-overboard scenario that allegedly gave rise to the whole Black Dog brand), to the presence of Mr. Douglas himself onboard, seemingly aware of every batten or inch of rigging. 

The work of running a topsail schooner was shared among all hands on board, but so too was the wonder. As former mate Gary Maynard put it: “The reward was the vessel. And that’s very 19th century.”

For the many passengers who have paid for their cabins and the experience of going to sea in a wind-driven vessel, this is the Shenandoah book of their fondest memories. Here are the tales about how Mr. Douglas got married, built a tugboat and built a restaurant all in the same year.

“I was bored or something,” he comments wryly in the book. “One of those things would have been enough to keep anyone busy.”

There are also many of the adventures craft and crew have experienced over the decades.

One bracing note sounded again and again throughout the book is a reminder of the hard and sometimes boring work that goes into sailing a schooner. The joy and freedom of seagoing is celebrated throughout, but readers are always aware of hard circumstances, ever-present dangers, and, maybe most unnerving of all, the non-stop exhaustion of round-the-clock watches and 20-minute cat-naps. 

The book is oversized in order to maximize its collection of illustrations. These are not only snapshots of Mr. Douglas, his wife Charlene, and some of the hundreds of people who’ve served as mates, riggers, boatbuilders, roofers and masters over the years, but also numerous portraits of the Shenandoah herself decade after decade, under all array of sail, against all kinds of backdrops. 

This living schoolroom for generations of students has long needed just exactly this kind of loving tribute. As Mr. Douglas’s friend and fellow captain put it, “Every fifth-grade class on Martha’s Vineyard has been able to sail for a week and tread on the oiled pine decks of their own clipper schooner for the last few decades, changing lives for the better every time.” 

My Shenandoah joins the long list of affectionate tribute-volumes sailors have written over the centuries to certain captains and certain ships. There’s a magic to such volumes, and Mr. Cabral has captured that magic perfectly here.