I didn’t set out to learn sailing like a man signs up for a class. Nah. It crept up on me the way the tide does when you’re not paying attention. One minute I’m living my life on land, the next I’m tossing a duffel aboard a 74-foot square-rigger called Stone Witch and pretending I belong there.
Truth is, I never really left.
That old girl, she wasn’t polished. No engine humming below, no fridge stocked with cold luxuries. But don’t mistake that for some purist nonsense. I like my comforts as much as the next sinner. Give me cold beer and a soft berth any day. What made Stone Witch magic wasn’t what she didn’t have. It was what she gave.
Three months running the Pacific side of Central America will carve something into your bones that never quite washes out.
And somewhere along that stretch, under a sky that looked like it had been spilled out of a jewelry box, I had what you might call a religious experience. Not the church kind. No pews, no hymns. Just salt air, moonlight, and the quiet understanding that you’re a small piece in a very big machine.
It was my watch, middle of the night. Three in the morning. That hour when time feels like it’s holding its breath. My girl was below catching some sleep, and I was alone with the helm, the wind barely enough to keep us moving. Three knots, maybe. Just drifting south like a thought you haven’t finished yet.
The moon had laid a silver highway across the water, stretching out to forever. I was staring into it when I heard a sharp breath beside me. Snapped me upright.
There he was. A dolphin. Just cruising along like he had somewhere to be but wasn’t in a hurry to get there.
And for a moment, it felt like we were cut from the same cloth.
Yeah, yeah, I can hear the landlubbers already. Sounds like a cheap paperback, right? But out there, miles from anything that resembles “normal,” things get real in ways you can’t explain over a barstool.
I leaned back, one arm steady on the tiller, and every time I glanced over, that dolphin would rise just enough to take a look at me. Not random. Not accidental. It felt deliberate. Like we were checking in on each other.
Call it imagination if you need to sleep better at night. Out there, it felt like conversation.
And here’s the thing most folks never understand. It’s not about words. That dolphin didn’t speak English, Spanish, or anything you could scribble in a dictionary. But there’s something deeper than language moving through that water. Something that doesn’t need translation.
Any sailor who’s spent real time offshore knows exactly what I’m talking about.
I’ve been close enough to whales to see the scars on their backs. Close enough to feel the push of water as they pass. Off Mexico. Off Hawaii. Moments where you realize you’re not observing them. You’re sharing space.
There’s a connection there. Ancient. Unspoken. Real.
Like the old line from William Shakespeare reminds us, there’s more going on in this world than we ever bothered to explain.
Years of roaming the oceans stack up encounters like driftwood. You don’t forget them. You carry them.
Off Makena Beach in Maui, we dropped anchor and ended up spending six hours with a humpback family. A big male, a cautious mother, and a calf that looked like it was still figuring out how to be a whale. They circled us, slow and deliberate. You could almost see the lesson unfolding. “That thing floats. Stay clear.”
Out by Catalina, I once spent an afternoon diving with a harbor seal that decided I was worth its time. We played. Not metaphorically. Not poetically. Actually played. Ducking, weaving, hiding behind rocks like a couple of kids who never learned to grow up.
And off the Big Island, I reached out toward a humpback mother. She turned, slow and powerful, and gave me a warning with her tail. Not aggressive. Just clear. “That’s close enough.” Then she circled back, almost like she was making sure I got the message without getting hurt.
You don’t walk away from moments like that unchanged.
In the BVIs, tucked into Little Harbor on Peter Island, a pair of dolphins decided we looked interesting. What started as curiosity turned into hours of swimming, circling, leaping. They weren’t just passing through. They were engaging. Like we’d been invited to something we didn’t quite deserve but were welcome to enjoy anyway.
And night after night, watch after watch, you see them. Dolphins, whales, shadows that move with intention. They come alongside, match your speed, and every so often, they turn and look up at you.
Not past you. At you.
Look into that eye sometime. Really look. It’ll rearrange your understanding of things in a hurry.
Because here’s the truth they don’t print in brochures.
When you head out to sea, you leave behind the kingdom of man. Out there, we’re not in charge. We’re visitors. Guests in a place that doesn’t belong to us.
And the locals? They notice how you behave.
You move with respect, you feel it returned. You act like you own the place, and the ocean has a way of reminding you that you don’t.
There are folks who stare out at the horizon and can’t imagine why anyone would trade solid ground for all that uncertainty.
And then there are the rest of us…
…who can’t imagine how anyone could stay.
