Homeschooling while traveling on the high seas

For Carolyn and her family, homeschooling is more than just schoolwork—it’s an adventure. Living on their yacht Moon River and sailing through Southeast Asia with their four boys—Jackson (13), Tasman (11), McKinley (9), and Hawken (7)—they’ve turned the world into their classroom. In this chat, Carolyn shares what it’s like homeschooling while traveling, how the boys are learning in the real world, and how tools like Start Right Workbooks and LearnWell Digital keep everything on track, even when the waves are rocking!

Setting sail and homeschooling while traveling

Hi Carolyn, can you tell us a bit about your family and how you ended up combining homeschooling with sailing around Southeast Asia?
We’re a family of six—myself, Richie, and our four boys. We spent six months in 2019 sailing around Tonga, Fiji, and New Caledonia, which was an incredible experience. At the time, Hawken was only 2! After that, we lived aboard in Auckland for a few years while we got ready for this bigger adventure. I’d already been homeschooling during Pacific trips and various lockdowns, so when we started planning for this journey, it felt like the right time to set sail as a family. It’s been such a fun way to learn together.

What are some of your main goals for your boys' education during this journey?
Well, above all, I want my boys to feel like their education isn’t limited by our decision to homeschool. I was nervous at first, thinking I’d be taking on too much responsibility, but now I’m totally passionate about it. It’s not always easy, but the best thing about homeschooling is being able to let them dig deeper into things they’re interested in—watching their excitement grow when they get into something. And of course, being surrounded by new places means we get to draw inspiration from what’s right outside our door.

Hands-on learning: passion projects on the go

I bet the boys get pretty inspired by their surroundings! Any cool passion projects that stand out?
Oh, absolutely! One of my favourites was when we arrived in Papua New Guinea. We went through our flags to find the PNG flag to fly from our mast, and that turned into a whole study on flags—what makes a good flag, how they're designed, and then they each created a new design for Moon River. Another time, we visited a Buddhist temple, and it sparked a huge interest in learning about Buddhism, which led to a big project. And when the fan on the boat broke, it turned into a whole lesson about how electric fans work—how to fix them, find the problem, and even re-solder a faulty connection. It’s amazing how hands-on learning happens without me even having to plan it!

That sounds incredible! What’s been the most surprising part of your adventure so far?
We had the most amazing morning diving with whale sharks. They were gentle giants, and it turned into such a rich learning experience. Afterward, the boys painted watercolours of the sharks, and we even submitted our photos to a citizen science program. One of the sharks we saw turned out to be a previously unidentified individual (their star-like markings are unique identifiers), which was pretty cool. We also learned some awesome mythology about whale sharks from different cultures—there are so many beautiful names for them in other languages.

Start Right Workbooks

How did you first come across Start Right Workbooks, and how have they helped with your homeschooling while you’re on the move?
I actually heard about Start Right Workbooks from another sailing family. I was looking for a resource that would follow the NZ curriculum but also allow the boys to work independently, especially when we’re offline or in remote locations. Start Right Workbooks have been perfect—they’re clear, easy to follow, and have full worked examples, so the boys can get through the work by themselves. The workbooks really help them stay on track, even when I can’t be right there to guide them.

 

The challenges of homeschooling while traveling

What’s been the hardest part of homeschooling while traveling?
I think the biggest challenge, no matter where we are, is keeping the boys motivated when it comes to the subjects they’re not as interested in. You know, the stuff that feels like work! And living on a yacht can be tough when we’re all packed into a small space—sometimes it’s hard to work through a tough problem without distractions or finding a quiet spot for one-on-one attention. But we make it work, and they’ve learned to help each other when I’m not available to sit with them.

How do you keep them engaged and motivated while sailing?
Some days are easier than others! When we’re in places where they can surf or explore once school is done, it’s pretty easy to keep them focused. But then there are the days where getting through schoolwork feels like a struggle. My 7-year-old, Hawken, for example, loves maths but isn’t too keen on writing, so getting him to stay on task can be tricky. What’s really cool is how much they’ve learned about the ocean, weather patterns, navigation, and even conservation—all things they pick up just by living on the water. They also have real responsibilities on the yacht, like managing our water and fuel supplies, which gives them valuable hands-on learning experiences.

Exploring local culture

I love that they get to learn in such a practical way. How do you bring local culture into your learning?
Before we arrive in each country, we study it—learning about its geography, language, history, and culture. But the real magic happens once we’re there! We buy fresh produce from local markets, meet local kids, and even trade with villagers. One of my favourite memories was celebrating Indonesian Independence Day with a local family. We got to take part in the festival, enjoy the food, and learn some traditional dances. Those real-life experiences are the kind of learning that textbooks just can’t offer.

Can you tell us about a memorable learning experience from your travels?

Definitely! We had a wild day in a small village on Buru Island in Indonesia. Hawken invited the local English teacher and a group of kids to our yacht for an English lesson. The next day, Richie ferried 38 kids—along with 30 ukuleles—onto the boat for an impromptu class! We taught English, learned Indonesian words and had a mini ukulele concert. Then, of course, we ended the day with canoe races and diving off the bow. It was a total adventure, and one of the best homeschool days we’ve had.

Homeschooling while traveling and still keeping track

How do you keep track of their progress while homeschooling on the go?
We haven’t done the best job at tracking their progress with formal tests but using Start Right Workbooks gives us a good indication that they’re working at the right level. The books are laid out in a way that shows they’re mastering the material, and I can always tell when they’re ready to move ahead. In the future, I’d like to incorporate more testing or reviews to keep track of where they’re at.

What do you think of the LearnWell Digital resources you’ve tried so far?
We’ve really enjoyed using the LearnWell Digital resources, especially for science. The boys love them because they’re easy to use and really engaging. The beauty of digital resources is that they allow the boys to work independently, and since we’ve added Starlink to our boat, we’ve had great internet coverage almost everywhere, which makes using the resources a lot easier.

Tips

Finally, what advice would you give to other families considering a similar homeschooling approach while traveling?
I think the biggest thing to remember is that traveling adds a whole new level of stress and excitement. Not every day is going to be a “perfect” homeschooling day. Some days, it’s okay to ditch the bookwork and just go with the flow—there’s so much learning that happens off the page. If you try to push too hard on tough days, it can lead to frustration. Flexibility is key—let the adventure and learning happen in a more natural, relaxed way.

 

Thanks so much for sharing with us, Carolyn.  We have loved hearing about your incredible adventures. Your story is such a great reminder of how education can happen everywhere, and at any opportunity.

If you're like us and want to keep following what happens with Carolyn and her family as they travel, you can visit @chasingmoonriver on Instagram or their website.