Confessions of a Yacht Delivery Captain: Stories Over the Horizon

Before and during the columns, the broadcasts, and the books, I was delivering yachts. For a stretch of years, one of the ways I made my living on the water was as a yacht delivery captain — moving vessels for owners who didn't have the time, the crew, or sometimes the confidence to bring a boat from one port to another themselves. It's a line of work that doesn't get talked about much, and it gave me some of the best stories I've ever collected. This is an overview of what that life was like.

What a Yacht Delivery Captain Actually Does

A delivery captain is hired to move a vessel from Point A to Point B — sometimes a few miles up the coast, sometimes a thousand miles or more through open ocean. The owner hands you the keys to a boat that's often worth more than a house, and they trust you to bring it back in one piece. You inspect it, provision it, plan the route, watch the weather, and put the hours in underway that the owner can't or won't. It sounds simple. It is not.

The Pre-Departure Ritual

Every delivery begins the same way: a thorough going-over of the vessel. You check the rigging, the engine, the through-hulls, the safety gear, the electronics, the fuel, the water. You find the things that aren't right and you fix them before you leave the dock — because out there, a loose fitting or a tired pump becomes a real problem. I learned more about boats in those pre-departure hours than from any course I ever took.

Reading the Weather

On a delivery, the weather is your boss. You study the forecasts, you watch the barometer, you read the sky and the sea. Sometimes you wait. Sometimes you leave at three in the morning to catch a weather window that won't last. The hardest lesson of delivery work is knowing when not to go — and having the discipline to stay tied to the dock when everything in you wants to be underway.

The Long Hours

Deliveries are mostly about endurance. Watches on and off, day and night, sometimes for days at a time. You learn to sleep in twenty-minute intervals. You learn to eat when you can, not when you're hungry. You learn that the ocean at night, alone on deck, is one of the most beautiful and lonely things a person can experience. Those hours are where the material for my upcoming book, Salt, Stars & Secrets: Confessions of a Yacht Delivery Captain, really came from.

The Characters

You meet everyone in this work. Anxious owners who want to come along and shouldn't. Experienced delivery crew who can hand-steer for twelve hours without complaint. Dockhands in strange ports who become fast friends. The occasional charter captain who's been running the same route since before you were born and knows every shoal by name. The people are as much a part of the story as the passages.

The Things That Go Wrong

I've had steering fail offshore, sails tear in building wind, engines quit in the wrong place at the wrong time, and once, a bilge pump that decided to stop working at the worst possible moment. Every delivery captain has a list like this. The job isn't about avoiding trouble — it's about handling it calmly when it finds you. That's what the owner is really paying for.

Mainland to Hawaii

The coastal runs were one thing; the Hawaii deliveries were another entirely. Taking a boat between the mainland and the Islands is roughly two thousand miles of open ocean, and once you're past the last headland there is no pulling in for repairs, no shelter from a blow, no help coming for days. You provision for everything — fuel, water, food, spares — because what you leave the dock with is all there is. You watch the Pacific weather fax and the gribs like your life depends on it, because some days it does. The tradewinds build, the swells stack up, and the boat settles into a rhythm that can last a week or more. Then, on a clear night far from any shipping lane, the sky opens up in a way you will never see from land — stars so thick you feel like you could reach up and run your hand through them. That sight, more than anything, is what stayed with me from those passages, and it's a good part of why the book is called Salt, Stars & Secrets.

Funny Shoreside Stops

Not every memorable moment happened offshore. Some of the best stories came when we finally made land — gassed up, grabbed a meal, and let the crew breathe. There was the fuel dock in a sleepy harbor where the dockhand insisted on telling me his life story while diesel slowly overflowed onto the deck. The marina where the only restaurant for miles was a bait shop with a single picnic table, and somehow it was the best burger of the whole trip. The night we limped into port after a rough passage and the whole crew fell asleep sitting upright in a diner booth before the food even arrived. Shoreside stops were where the tension came out of everyone — where a cold drink and a hot shower felt like absolute luxury after days of salt and watch-keeping. Those landfalls, and the odd characters waiting at every one of them, are half the reason I still laugh about those years.

Why I Still Value Those Years

Delivery work taught me seamanship in a way no other part of my career has. It taught me patience, judgment, and a healthy respect for the ocean that I carry with me every time I leave the dock — whether I'm delivering someone else's boat or just taking friends out for an afternoon. Some of the best stories I've ever told on the radio and in print started on a delivery, and I'm looking forward to telling the rest of them in the book.

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