When 2020 hit, my event-planning job came to a standstill—3,000-person wine festivals weren’t exactly pandemic-friendly. Meanwhile, my husband, Bo, was working from his laptop, so I started joking that we should "just move to Hawaii!" What began as a joke turned serious when Bo said, “If you can make it happen…” Two weeks later, after decluttering every room and renting out our home, we were on a flight to the islands.
That three-month trip was the spark. We realized we could work from anywhere and didn’t need to limit ourselves to a one-week “vacation”.
The Planning Process
Inspired by travel-nomad families like the Bucket List Family, we spent the next three years saving, planning (a lot), and shifting our mindset. My first tip? Start telling people you’re going to do it—even if it feels wild at first. Soon enough, you’ll start believing it yourself!
Then came logistics. We chose a five-month window where work was slower and school breaks aligned, planning for 3-4 weeks in each country to balance work, homeschooling, and adventure. Our route took shape as we swapped travel tips with friends and used an around-the-world (ATW) flight program. This ticket was a game-changer—more cost-effective than separate tickets, with expert guidance, and all flights booked at no extra cost. As long as we kept moving East or West without backtracking, we were good to go.
We balanced pricier countries with more affordable ones, making the most of our travel budget. Chase Preferred points were a huge help (highly recommend for travel perks!), covering hotels, smaller flights, and lounge access, which made long airport days so much easier.
Finding Balance – Working and Schooling on the Road
People often asked what it was like traveling with kids, and honestly? It’s just like parenting at home, but with a new backdrop. There were ups and downs, but it’s funny how time makes the tough days fade. All the photos capture those once-in-a-lifetime moments, and in the end, that’s what sticks with you.
Early mornings became our lifeline, giving us 2-3 hours of focused work time before the boys woke up. Afterward, I’d handle schoolwork with them while Bo continued working. Our school was incredibly supportive, with teachers and the principal ensuring we had the resources to stay on track. IXL became our 4th grader’s go-to for online studies, while our kindergartener traveled with his workbooks. By noon, we were usually free to explore.
To keep everyone engaged, we balanced our outings with activities we’d enjoy, adventures for the kids, and something educational. Every destination became a classroom, and local museums were a must. Now, when they learn about these places in school, they’ll have a personal connection that makes it even more memorable.
Our boys have climbed the marble steps of the Colosseum, stood in awe before The David, cage-dived with great white sharks, and hiked Lion's Head in South Africa. They learned about freedom fighters in India, gazed up at the Taj Mahal, and discovered the reality of animal cruelty at a Thai elephant sanctuary. They sailed beneath Sydney’s iconic bridge, sheared a sheep in New Zealand, and so much more.
With each new country, they picked up the basics of new languages, learning to connect even with a few simple words. They began to see how different, yet similar, people are across the world, experiencing a level of human connection you just can’t teach from a book.
The Realities of Family Travel – The Ups and Downs
Every country brought its own challenges, from mastering time changes and adjusting our schedules to working at odd hours — to watching the kids struggle with the lack of Western comforts they’d grown used to. Each destination required adjustments, and the boys had to learn to adapt.
It was far from perfect, and many lessons didn’t come full circle until we were back home. Over time, I noticed real changes in my kids. They weren’t as picky about food, could handle going with the flow, knew how to eat out without needing a device, and could connect with kids of any age—or even adults—with good manners and meaningful conversation. Now, let’s be real: this isn’t them all the time (a mom can dream, right?), but the difference was undeniable.
Travel also strengthened their brother bond and brought us closer as a family. When tough days came, we only had each other to lean on, and that created a resilience that’s stuck with us. Now we “laugh” about those hard days—like when Davis sprinted through an airport terminal begging the gate agents to hold the plane while the rest of us raced behind him. Or the time Bo filled out a visa with one wrong number, stranding us in Johannesburg for four extra days while waiting for approval to continue to India.
These moments taught us valuable lessons: that each day is what you make of it, that grace for one another is essential, and that you shouldn’t be afraid to try new things—even when they don’t go as planned.
One of the greatest joys of this journey was exposing my kids to different cultures. They loved learning the basics of each language—just enough to say “hello” and “thank you.” It’s a small effort, but I can’t recommend it enough. A few key phrases go a long way in connecting with locals and show that you’re genuinely interested in their culture, not just checking off tourist attractions.
And the food? Unforgettable. My kids still talk about Sid’s incredible omelets in India, the scorpions we tried in Bangkok’s Chinatown, and the turmeric health shots in Bali. These experiences weren’t just about tasting new things, they were about immersing ourselves in the everyday life of the places we visited.
Everywhere we went, we made friends who welcomed us with open arms. Those connections have become priceless, and we often talk about visiting them again someday.
Takeaways – How Travel Shapes You
The biggest lesson I took away from our travels is how much clearer my mind felt while abroad. Life didn’t feel as overwhelming, even though I still juggled work deadlines, laundry, and dinners. The difference was in the pace. We had a plan each day, but it was flexible, and most of the time, we did what we truly wanted. There were no endless schedules packed with practices, events, and obligations. That slower pace shifted my mindset and taught me to be more present.
Another surprising takeaway was a renewed gratitude for being an American. The things we often complain about here aren’t even possibilities in many countries. Access to clean water, air conditioning, and a safe home to raise your family? That’s a privilege—not a guarantee. I came back with a deeper appreciation for the blessings we sometimes overlook.
I also realized how much we have in common with people around the world. There’s a misconception that Americans are disliked everywhere, but we never felt that. People welcomed us with kindness and open hearts. One of the most beautiful things about traveling is connecting with others, and those interactions became some of our favorite memories.
For example, in Florence, the boys played soccer—or “football”—with a group of kids who didn’t speak the same language. One was Chinese, one German, and two Italian. Yet, through body language, smiles, and a shared love for the game, they connected instantly and played like lifelong friends. Moments like that showed us that no matter where you’re from, we’re more alike than different.
Travel taught us empathy, resilience, and adaptability. It showed my kids how to embrace differences, work through challenges, and see the world from perspectives beyond their own. It gave us a real-world education that no textbook could provide and showed us that wherever you go, kindness and curiosity go a long way.
Travel might seem out of reach, but with a bit of planning and courage, it’s more accessible than you think—and it can be truly life-changing for your family. It’s not about having the perfect trip; it’s about stepping out of your comfort zone, embracing new experiences, and learning together. The memories you make, the lessons you learn, and the connections you forge will stay with you long after you’ve unpacked your bags. So dream big, start small, and let the world become your family’s classroom.
The memories you make, the lessons you learn, and the connections you forge will stay with you long after you’ve unpacked your bags.