How does school happen in this cruising lifestyle? The truth: it doesn't.

Del Viento- dock

This picture is a perfect example of the serendipitous nature of the learning that does happen. I walked past these two twenty-somethings on the way to Del Viento one afternoon. They were lying on the dock about ten feet apart with their heads and arms hanging over the edge. I interrupted them: “Are you guys marine biologists, by chance?” They told me they were and wondered how I guessed. I told them I have two girls who would spend all day in the same position if we let them. I introduced Eleanor and Frances to them and the four of them looked at the water and talked about stuff in the water for two hours. The girls love that stuff and know a lot. Windy Robertson

“Well you get it, right? I mean, it would suck to be a boy named Sue.”
“Because it’s a girl’s name.”
“But why did that help him?”
“Because it made him tough, he had to fight people who teased him.” I watched Eleanor’s face for a flash of understanding. There was nothing.
“But why did he need to be tough?”
“Because the world is tough, because life is tough. His dad wanted his son to be tough and he knew he wouldn’t be around to help him get tough.”

I heard my own words and how they must sound to my nine-year-old. I was learning about her perspective at the same time I was trying to teach. She had no context. Maybe I should retract and start over, I didn’t want her to think people get tough or benefit for being bullied and teased.

She interrupted me before I could detour to explain that a real-life Sue may indeed have grown into a tough-looking man, but that beneath the muscles and tattoos he may not be tough in the ways that matter, in strength-of-character, in the strength to be vulnerable. “But the world’s not tough.” She said.


“Okay, no—I mean yes, it sure can be, you’ll see. But the point is that the song is meant to be a funny story, an oversimplification using ideas from another place and time.”
“Like the Old West?”
“It was written by Shel Silverstein.” Windy added. She was tucked in the corner with her iPad, now offering color commentary from her Offline Wiki app.
“Shel Silverstein wrote ‘A Boy Named Sue’?” I knew this would pique Eleanor’s interest.
“Can we hear it again?” Eleanor asked.

And we did hear it again, that song and the entire “At San Quentin” album.

Until she was eventually distracted, we’d talked about how Cash’s practiced dialogue between songs appealed to his uniquely homogeneous audience, about how politicians and others pander, about Cash’s prison tour, and about June Carter Cash and the Carter Family.


The biggest question from folks contemplating cruising is How much does it cost?

I’ve addressed that question here before: Cruising doesn’t cost anything in particular, there is no price tag on the lifestyle. I can tell you what we spend, but that information will only inform your own estimation.

But I haven’t addressed the biggest question for families contemplating cruising. They all want to know, “How will schooling happen?”


Here is the answer: It won’t, there is no school in this lifestyle. I can tell you how our kids are learning, but that information will appeal only to like-minded parents.
In the past couple years, we’ve seen almost as many approaches to learning aboard as the number of cruising families we’ve met. I have no basis for qualitatively comparing or assessing them. Who can? All of the approaches look very different from a traditional, institutionalized education model, and that’s a point worth emphasizing.

Our steady travel prohibits our kids from regularly attending school. They are denied access to many rich aspects of that experience: the long-term teacher relationships, the sports teams, the clubs, the labs, the other students and the classroom interplay, and the millions of incidentals that are a product of that environment.

We’re okay with that. You have to be if you plan to do this long-term.


Currently, our approach to education is little more than active, involved parenting. It’s the same thing millions of folks do every evening when the whole family is together, we just do it at all hours—and in some pretty interesting environments. At most, the girls spend 10-20 minutes a day on formal “schoolwork,” stuff like math apps on the iPad or handwriting workbooks. The bulk of their education comes from their reading, their pursuing their interests in their unique, ever-changing world, and many, many seemingly insignificant—sometimes trivial—engagements with us, like the above.

But we’re done with San Quentin and the Man In Black. I think that after breakfast tomorrow, while Frances clears the table and Eleanor does the dishes, we’re all gonna take a loud ride on the Crazy Train with Ozzy and see where that takes us. All aboard girls…ha, ha, ha, ha.


I__n our twenties, we traded our boat for a house and our freedom for careers. In our thirties, we slumbered through the American dream. In our forties, we woke and traded our house for a boat and our careers for freedom. And here we are. Follow along at