“Do we have any milk?” she asked, standing in the galley, a blue plastic cup in her hand. How could I have been surprised, since this was her third morning in a row making that request? We were on a training run to California’s Channel Islands with a crew of nine students on a chartered 65-footer. We had left San Diego days earlier and hadn’t stopped as we clawed our way north on an indirect path to San Nicholas, a weatherbeaten island near Point Conception. There was no milk onboard when we departed, and the situation hadn’t changed. Yet, every morning came the question. It was as if she thought we had made a quick but secret dash to a 7-Eleven in the middle of the Pacific or maybe had stashed a cow in the lazarette.

Crews can be tricky if they’re new to sailing, when there’s a strong but inverse relationship between expertise and expectations. An unrealistic and often inflated assessment of one’s skills is also part of this phenomenon, especially if an individual holds an influential or prestigious job on land.

Leaving Bequia in the Grenadines one day, I had a crewmember suggest that we all “take turns being captain” in a responsibility-be-damned version of a game show. Perhaps this idea was based in his need to stir the pot; he confessed to enjoying confusing pizza delivery people when he called in a pie from his Catalina 25, which was hauled on a beach in Lake Tahoe. To appease his need to lead, I put him in charge of raising the main on our 50-foot cat in Admiralty Bay that morning. We just about ran out of water as we motored slowly forward and had to turn from the fast-approaching shoreline before he figured out the lines, coordinated the crew, and barked orders. And that bay is huge.

Patience is often the best way to deal with unrealistic or pot-stirring crewmembers. On a breathless day off the coast of Athens, a self-proclaimed “true sailor” in the group demanded that we sail rather than motor back to the harbor as he donned his sailing gloves. The breeze was gusting to 4 knots. We raised the sails on the heavy 50-foot monohull and sat, flapping in the breeze downwind of the stinky island of Methana. Hidden behind my sunglasses, I pretended to nap in the cockpit while observing the mayhem. The next 20 minutes were video worthy as the mutiny formed in fits and starts until the group subdued the “true sailor” and motored quickly back to the marina before sunset.

If the issues aren’t a danger to the boat or crew, I find it best to let things glide along at their own pace and in their own direction. I confess, sometimes I enjoy the drama. One woman insisted on “throttling the gears” just like her boyfriend had taught her on his Carver 38 powerboat. I never figured out what she meant by that, but she was convinced this was the answer to managing our single engine whether docking, anchoring, or when she was just standing at the wheel. Each evening, she dipped into her contraband liquor and when properly emboldened, she would pursue a single male crewmember around the deck. The poor guy jumped into the dinghy for “an excursion” every chance he had.

I have a different crew on just about every charter, so I see a lot of personalities, some of them not at their best. For me, it can be exasperating trying to keep the boat moving while teaching new skills, or it can be an entertaining exercise in group dynamics. Regardless of whether it’s demanding captain hopscotch or expecting unprovisioned milk to miraculously appear on a nonstop sail, charter crews can be a handful. It’s usually best to lean heavily on humor and let the crew sort it out among themselves. They eventually tire of the antics of one of their own and do the trickiest part (crew management) of a captain’s duties for you. 

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October 2024