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NIKKI HENDERSON

Yachting World

|

November 2025

THERE MIGHT LATER BE AN OPPORTUNITY TO REDEEM YOURSELF, BUT SOMETIMES BEING A SKIPPER MEANS MAKING UNPOPULAR CHOICES

NIKKI HENDERSON

Most people agree: skippers are responsible for the safety of the crew and the boat. But the job far exceeds keeping everyone alive and afloat. A good skipper also has to deliver an experience. One that aligns, at least partly, with the expectations of the crew. In my view, that's the most overlooked and arguably the hardest part of skippering.

For commercial skippers 'experience provider' is literally on the job description. Crew sign up to a defined trip, often with a detailed itinerary, and they pay for their place on board. The task is to keep a group of strangers safe, meet their expectations and finish on time. Sounds tough? It is. But it isn't just a commercial skipper's problem. Every crew, even friends and family, come aboard with expectations. In fact, I sometimes think delivering an experience to strangers is easier than doing it for loved ones. At least if I disappoint paying customers, I don't have to hear about it for the rest of my life.

I recently had one of these crews join me for a cruise from Alaska, USA to Victoria, Canada. They wanted wildlife encounters, a taste of Pacific Northwest sailing, and some kind of 'offshore' experience. In seven days I needed to deliver overnight sailing, coastal cruising, a remote wilderness anchorage, and a 600-mile passage.

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