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Sailing Charter News

Three people sail a small boat in tropical water near shore.

Charter: Where are the Best Places?

As soon as anyone learns that I’m a charter captain, invariably the question comes: “Where’s the best place to charter?” If you’ve ever read TripAdvisor or Expedia reviews, you’ll note that “best” means a lot of things to a lot of people. I know that whatever answer I give, it ...read more

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Charter: Group Dynamics

“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 ...read more

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Charter: Day One Damage Control

The first day of any charter means a mountain of responsibilities for the skipper and extended periods of hurry-up-and-wait for the rest of the crew. It can be a long, boring day for friends or guests hanging around, sweaty and anxious about starting their vacation after a long ...read more

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Charter Ownership: Changing the Horizon

Jamie Brown had always nurtured a dream of sailing a transatlantic. He thought he’d have to wait until he retired, and then he’d spend ages preparing whatever boat he had chosen before actually doing the thing. But it all happened a lot sooner than that, and in a manner he’d ...read more

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Charter: It Takes What It Takes

It was October, and Hurricane Maria had just stomped over Les Iles Sainte, devastated Dominica, and was still cooking up 12-foot seas and 25 knots of wind in the Caribbean. Of course, I hadn’t anticipated this when I signed up four months earlier for a delivery charter of a boat ...read more