Sailing the World as a Nomad
Nomad Profile
Matt is a sailor, storyteller, and cybersecurity tinkerer. He left the corporate grind to circumnavigate the globe by hitchhiking around the world on sailboats—sailing 30,000 miles across oceans without ever owning a boat.
He writes about sailing, technology, and the absurd intersections of adventure and everyday life. He is the author of Global Hitchhiking (I just bought it!), and the voice behind the podcast Latitude Longings. You can follow Matt’s writings at Living Large By Living Little on Substack and the web.
9 Fun Facts
First Name: Matt
Age Range: 60s
Nationality: US
Nomadic Stance: For 3 years, from 2016-19, was Full-time (called it my mini retirement). Currently working towards buying a boat and becoming full time again.
Last Corporate Job: Technology company
Current Job: Part-time technology, Day Trader
Favorite Country: St Helena
Next Stop: Wherever I find my boat to start
What do you like best about the nomadic life? Adventure
2 Questions
1) If people want to sail and see the world (”global hitchhiking”), what is the best tip you can give them?
The best tip I can give is to learn a little bit about sailing before you go. You don’t need to be an expert, but understanding basic sailing terminology and concepts will help convince a captain that you’re serious. Learn things like points of sail, the difference between port and starboard, and where the bow and stern are located. If a captain asks you to go forward to the bow or trim a line, you’ll at least have a basic understanding of what they’re talking about.
Experience helps too. One of the best ways to get it is through a local sailing club. Even if you live far from the ocean, many lakes have active sailing communities. Racing events often need extra crew, and sometimes they’re happy to take on beginners. You’ll learn a tremendous amount simply by spending time on boats and being around sailors. Look for local sailing courses as well. You might be surprised how many opportunities exist, even in places nowhere near the coast.
Most importantly, don’t wait until you know everything. Nobody starts as an experienced sailor. A little knowledge, a willingness to learn, and a positive attitude will take you much farther than you might think.
2) You talk about visiting a country twice. What does this mean to you, and why is it important?
For me, visiting a country twice means experiencing it once in person and then revisiting it later through its history, culture, and stories.
When I travel, I’m often focused on the immediate experience—meeting people, finding transportation, exploring new places, and simply living in the moment. Years later, I find myself reading about the places I’ve visited and discovering things I completely missed at the time. That’s when I get to visit them a second time.
A good example is Malaysia. While sailing around the world, I ended up living there for eight months while waiting to find another boat heading west. During that time, I traveled extensively throughout Southeast Asia. More recently, I took a deep dive into the history of Malaysia and the Strait of Malacca and learned how important that region was to global trade for centuries. I discovered how trade routes helped spread Islam throughout the area and learned more about the impact of colonialism and Japanese occupation during World War II.
When I sailed through the Strait of Malacca, I knew it was busy. What I didn’t realize was that I was traveling through one of the most important maritime crossroads in history. Learning those stories years later gave me a deeper appreciation for a place I had already experienced firsthand. That’s what I mean by visiting a country twice. The second visit often adds meaning to the first.
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Christened “Wander Woman” by National Geographic, Erin Michelson has traveled to 135 countries & all 7 continents. She is a professional speaker and author of the Nomad Life™ series of curated trips and travel guides, including the #1-ranked Explore the World with Nomads.
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