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When the Student Is Ready: Charlie Deist on Learning to Sail

In the May issue of Latitude 38 Charlie Deist shared his experience of learning to sail under the instruction of Darrell Allen Caraway. The pair ended up creating a book of Darrell’s nautical paintings and text message instructions, called Three Sheets to the Wind: The Art of Spinnaker.

“You’re luffing,” said Darrell.

I looked over from the horizon toward the forestay and saw the jib flap a bit before it settled into a crisp, flattened curve.

My reply revealed my ignorance: “No, I’m not …. Wait, what do you mean?”

At 25 years old, I was a relative latecomer to sailing. It was my third or fourth lesson with Darrell Allen Caraway, my impromptu sailing instructor. I had approached him on Berkeley Marina’s J Dock after seeing him sail into and out of his slip effortlessly on multiple occasions. My recently acquired Columbia 24 had maybe been out once in the two months since I had arrived. That was still more often than most of my neighbors. It seemed as if Darrell was the only actual sailor around, and certainly the only competent one.

“You’re luffing again. You’re luffing. You’re luffing!” he shouted, as I nosed up even farther into the wind before finally falling off and back to a close reach. I didn’t mind getting berated from time to time. This sailing education came cheap. Sometimes we took my boat out and I paid Darrell in food or beer. Other times we took his boat, a Cal 20 rigged for easy singlehanding, and fittingly named Cheap Therapy.

It was in those four-hour sails just outside Berkeley that I gradually earned my sea legs. Once in a while I kicked Darrell $50 for his trouble, but I sensed that he didn’t do it for the money so much as to share a craft with a budding skipper who barely knew a beam reach from a broad. It may have helped that I greased his palm a bit, but my salty instructor friend seemed to get almost as much out of our joint sailing therapy sessions as I did.

As I learned the ropes — er, lines — Darrell lectured me with life lessons, and frequently ranted about his latest grievance. Among other monologues, I received a brief history of his architectural accomplishments around town.

“Of course, nowadays it’s all computerized,” he lamented.

As the architecture industry had changed, Darrell had refused to change with it — opting instead to hone his hobbies of painting, sailing, and restoring classic cars into a full-time lifestyle occupation.

Between gallery exhibitions in North Beach, he would set up his easel in front of East Bay shops, selling the paintings to the stores’ owners. There’s a rumor that the owner of Kingfish owns half a dozen of Darrell’s depictions of Temescal’s iconic Jamaican-themed pub.

Darrell Allen Caraway
Sailing and the waterfront inspire Darrell Allen Caraway’s artistic pursuits.
© 2021 Darrell Allen Caraway

You can read more at In the meantime, here’s a video of Charlie and Darrell sailing in celebration of their book.

Three Sheets to the Wind: The Art of Spinnaker will be available on Amazon as a hardcover.

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