"You're crazy!" That's what some people said when my wife and I decided to travel for three weeks, across three countries, with our three kids who were all under five.

Maybe they were right, but we believe in spending money on experiences and memories, not just stuff.

If you're unsure about a trip like this, let me tell you: it's totally possible and one of the best things you can do for your family.

This is the story of our trip.

Tokyo, Japan

Our adventure started in Tokyo, Japan, in August. This was a bad time to go; Tokyo was super hot, about 95 degrees. We stayed in an Airbnb in Ebisu which was a great spot for families.

A quiet residential street in Japan with a small child by a doorway.
A child resting on a bed in a rustic room with a paper lantern.

We visited Tokyo DisneySea, which is one of the most beautiful Disney parks I've seen. It's by the water, so you get a nice breeze.

Tokyo is an amazing city. But it seems made for families of four or less. With five of us, restaurants often didn't know how to seat us. They struggled to find a spot for our fifth person.

Here's an important tip: use a luggage delivery service from the airport. The only hard times were when we tried to move around the city with our suitcases.

Here are more pictures from Tokyo.

Crowds and children on a busy shopping street in Japan.
The family walking through a valley of rock formations.
Two young children holding colorful lollipops on a city street.
A travel selfie of two of the Sommers.
A child inside a colorful immersive light art installation.
A bright neon city street in Japan at night.

Bali, Indonesia

After Tokyo, we flew to Bali, Indonesia. This part of the trip was slow and relaxed. We stayed at another Airbnb in Ubud, and it was incredible.

Our best move in Bali was hiring a driver named Panda. He was amazing, and I'd tell anyone to hire him. Most travel in Bali is by scooter, so having a driver for our family was key.

We only planned one thing to do each day. We'd visit a nice beach resort, the rice paddies, the Bali Zoo, or the Monkey Forest. Then we'd go back home to relax.

My advice for Bali: really research where you're staying. Traffic is awful. A two-mile drive can take 40 minutes. Pick a central spot to cut down on travel time.

Children walking a wooden path through green rice paddies in Bali.
The Sommer family on a wooden walkway surrounded by jungle in Bali.
Children resting under a bamboo pavilion above the rice fields.
Two children watching birds beside a pond.
Two children looking at an orange koi pond.
A young boy on a stone path beside a carved statue in Bali.

New Zealand

Our last stop was four days in New Zealand. This was a huge change. We crossed the equator and went from summer to winter.

Children walking along a waterfront promenade with a city skyline behind them.
Children outside an everyday goods shop with a stroller.
Andy Sommer holding one of his children on a green hillside.
Two children standing by a lake among rolling green hills.

We stayed in an eco Airbnb in the mountains. It had no heater so we had to build a fire every night. The pace was very slow. We'd go to town, eat, shop, and then go home.

The best part was our drive to Hobbiton. My wife and I had been there eight years before and took a picture. This time, we took the same picture with our three kids.

A parent and child in the round doorway of a Hobbit hole at Hobbiton.
The family in front of a Hobbit hole at Hobbiton in New Zealand.

What We Learned

Traveling with kids gets easier the more you do it. And the longer your trip, the easier it gets. By the end of our trip, our kids understood the routine. They knew when it was time to get on the plane.

Second, change what you expect. This isn't a solo trip. We planned one main activity per day and left lots of time to just explore. Don't plan too much, or you'll get stressed.

Finally, don't overthink it. Travel means making memories. And those memories are priceless.

Building a life that allows for this kind of travel was a big part of why I left my corporate job. I share more about that journey in From Corporate Safety to Entrepreneurial Freedom.

Conclusion

Our three-week trip was full of different weather, cultures, and experiences. It showed us that family adventures don't need to wait until kids are older. Do them now.

We loved it so much that we've already signed our kids up for an international preschool exchange program in Japan next year. The world is big. And there's no better way to see it than with the people you love, no matter how old they are.

Thanks for reading! You can follow me on Instagram, TikTok, or Patron View for more updates.