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Five Years Driving Around the World as a Family

We Left Our Home Country 5 Years Ago to Drive Around the World

Earlier this month, we marked a milestone. It’s been five years since we left our home country, the United States, to begin our drive around the world.

Caspian Highland Full-time Overlanding Child

On October 9, 2021, we crossed the border from Eagle Pass, Texas, into Mexico. We were driving the 2021 Jeep Gladiator we ordered straight from the factory, then spent 45 days building in four different states. We had turned this Jeep pickup truck into the tiniest home on wheels. The three of us have called it home ever since. Caspian, who was four years old when we moved into Dauntless, doesn’t remember anything beforehand.

Potrero Chico Mexico Camping
Our first night in Mexico after crossing the border

It’s been a ride. We spent a lot longer in Latin America than anticipated, leaning into the hourless part of “Hourless Life.”

  • October 2021-March 2022: Mexico ๐Ÿ‡ฒ๐Ÿ‡ฝ
  • March-November 2022: Central America ๐Ÿ‡ง๐Ÿ‡ฟ๐Ÿ‡ฌ๐Ÿ‡น๐Ÿ‡ธ๐Ÿ‡ป๐Ÿ‡ญ๐Ÿ‡ณ๐Ÿ‡ณ๐Ÿ‡ฎ๐Ÿ‡จ๐Ÿ‡ท๐Ÿ‡ต๐Ÿ‡ฆ
  • November 2022-March 2025: South America ๐Ÿ‡จ๐Ÿ‡ด๐Ÿ‡ช๐Ÿ‡จ๐Ÿ‡ต๐Ÿ‡ช๐Ÿ‡จ๐Ÿ‡ฑ๐Ÿ‡ฆ๐Ÿ‡ท๐Ÿ‡ง๐Ÿ‡ท๐Ÿ‡บ๐Ÿ‡พ
  • March-September 2025: Mexico ๐Ÿ‡ฒ๐Ÿ‡ฝ
Our overland route through Latin America: 2021-2025
Our route through Latin America: 2021-2025

Four years in Latin America was not the plan, but life unfolded that way. Originally, we planned to return to the United States every two years to visit family and friends. But we ended up making more visits than expected in the beginning. We lost Eric’s mom while we were in Ecuador.

For all that time in Latin America, a part of all our hearts is there and maybe always will be. I miss hearing and speaking Spanish, a language I adore but butcher. I miss the people: their smiles, traditions, history, and deep attachment to family.

In January 2026, Dauntless made his way from Uruguay to South Africa in a container on a ship. His second time on an ocean (the first was crossing the Dariรฉn Gap between Panamรก and Colombia in 2022).

Montevideo Vehicle Shipping
Container Shipping of Vehicle in Montevideo

We flew to meet Dauntless in Cape Town and began our journey across a third continent. We’ve been in Africa since then. ๐Ÿ‡ฟ๐Ÿ‡ฆ๐Ÿ‡ณ๐Ÿ‡ฆ๐Ÿ‡ง๐Ÿ‡ผ๐Ÿ‡ฟ๐Ÿ‡ฒ๐Ÿ‡ฟ๐Ÿ‡ผ We’ve put down our deposit to ship to Europe in early 2027.

Caspian has visited two dozen countries in his nine years of life, most of which he drove all the way across (in the case of Argentina, the world’s 8th-largest country, he’s driven north to south, west to east, east to west, and south to north).

Hourless Life at Perito Moreno Glacier in Argentina
Perito Moreno Glacier, Argentina

Combining this international journey with the seven years prior we spent traveling full-time in the United States, we’ve been on the road for nearly 13 years. This means our relationship to travel is strange, abnormal. Travel is our normal. Instability and unfamiliarity are our constant companions.

And it is not easy. I think because the not-easy is also our normal, we don’t always realize when we are off-balance (I speak for myself). Stasis is tricky to find when everything around us is changing.

But in this, we grow. Constantly and deeply. Not in a linear way. With plenty of rollercoaster action, inside and out.

Jeep Stuck in Nicaragua

We love sharing our drive around the world with you. When in doubt, we always remember our family mission statement: Love. Explore. Study. Share.

This statement abbreviates LESS, emphasizing everything we’ve given up to gain what matters to us.

And as we share our adventure, we hope to inspire and empower you to see the world in a fresh way and act on what you learn. It’s a big, beautiful world out there.

Caspian Highland Author of Henry and the Hydra

Thanks for being part of our journey.

-B

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Written by:
Brittany Highland
Published on:
October 24, 2026
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Categories: Overlanding

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