Welcome!

We are the von Berg family- Cynthia, Waker, and our two daughters S, and E.
We know all about the ups and downs of family travel, from lost loveys to lost teeth!

von Berg Family at Zapata Falls, Colorado

When our girls were 6 and almost 4, we sold our house and started our family year out with a 60+ day road trip across the United States.

We’ve spent months road-tripping around the USA and Canada-exploring together and learning as we go.

We travel to make memories and spend quality time together as a family. We want our kids to learn to value experiences over things.

Read Next: Why I Travel- A Love Letter


Who I Am

I’m Cynthia, I fell in love with travel in my late teens, and have made it a priority ever since. Now I am a 40-something mother of two, who has visited over 40 countries.

I love showing my girls some of the beauty the world has to offer when we take the time to wander through it.

The Rest of the Crew

Originally from California, Waker lived in Germany for a year and has done his own share of traveling. When I met him he had just returned from exploring Peru and Machu Picchu.

Our girls S and E are learning to be great travelers. Sometimes they are adventurous, and sometimes they just need a good playground to get their wiggles out.

We are in the midst of a Family Year Out, sometimes called a Family Gap Year (what is that?). We started with a long cross-country road trip in the Summer of 2021, then went international in January 2022!

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How We Got Here

I’m a mom, entrepreneur, and passionate traveler. I started traveling with a backpack and a pair of Tevas on college breaks and fell in love with seeing the world.

Cynthia Pregnant in Bali
Babymoon in Bali

On the Road

I quit my first full-time, after-college job to go backpacking through Central America. It was the first time I chose travel over a more conventional life.

I joined a friend in San Jose, Costa Rica. We traveled south as far as the Panama Canal, then meandered slowly north. We slept in tents and bathed in the ocean. We ate fresh tortillas with jam and hiked every ruin we could get to.

Those were the days of slow internet cafes, and photos taken on 35mm rolls of film. Eventually, my sister picked me up from a dusty bus station in Los Angeles.


Back to Regular Life

After returning to the USA, I moved to New York City, earned a graduate degree, then eventually became Creative Director of a children’s toy brand.

But I never stopped traveling. I met up with a friend in Africa- together we climbed Kilimanjaro and then went on safari in Tanzania. I traveled solo through Argentina and Chile. I honeymooned in Thailand and Cambodia. I baby-mooned in Indonesia.

When my oldest daughter was born (S) we moved to Connecticut. We embraced having a backyard, access to a beautiful lake, and quiet country roads. My parents retired, and I took over as President of a specialty food e-commerce business.

S loved pointing out the cows on our drive to daycare and the rumble of driving through a real covered bridge. With a second daughter soon joining us (E), we continued to explore a bit closer to home. Out to California, down to New York City, to Boston, to Washington D.C.


The World Turned Upside Down

When the pandemic hit, we found ourselves confined, like the rest of the world, largely to our own home. School closed. Playgrounds closed. My business closed. We bought a canoe. We brainstormed treasure hunts through the backyard.

We started dreaming of a different life when things could get back to normal. I brainstormed a “Plan B” that involved a “family year out”, or “family gap year”. Slowly Plan B became Plan A and Sharing the Wander was born.

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