Travel Continuously as a Sailboat Captain, Here’s How.

I look out at the horizon as the sun dips lower toward the water.

The boat rocks peacefully, cutting through the water at a friendly clip. We have a perfect breeze, cooling down the end of a hot day. Suddenly, a Humpback whale appears, launching herself out of the water just two hundred feet off our port quarter. She spins gracefully and lands with a big splash. Moments later, her calf, a small whale jumps out of the water following mom’s lead. She comes closer and closer, practicing her breaches to the cheers of everyone onboard. What was already a perfect evening is now a night I will remember forever.

My name is Liz, I am 26 years old and I am a sailboat captain. I get paid to experience moments like these. Through my professional career in sailing I have been able to explore tropical places all over the world. I am currently travelling through Cuba, backpacking with money I’ve made from sailing. So, how did I land the ultimate job that allows me to do what I love AND gives me the ability to take months off to travel? Good question.

The simple answer is this: I take short contracts as a sailboat captain, make lots of money and then run away to travel as often as my finances permit!

travel plane

Growing up I went to high school in New York City. The narrative there was pretty clear: work hard in school so you can get into a good college, get into a good college so you can get a good job, get a good job so you can make lots of money, make lots of money so you can be happy. But when I graduated from high school in 2008, there was a global economic crisis that threw a major curveball in my family’s finances. Suddenly, student loan applications appeared, launching themselves at me like chains I’d have to wear for eternity.

Surprisingly, the idea of going to college became an open dialogue with my parents instead of something I was expected to do without question. I opted to take a year off to find myself, and found myself backpacking through Central America to the chagrin of most adults I knew. It was there that I fell in love with travel and realized that there’s no better education in the world. I wrote the same thing in my journal over and over, “how can I do this forever?” “How can I make this last?”

Flash forward two years later when I was working as a waitress and I was randomly offered a position on a sailboat headed south to the Caribbean from New York. Having spent an unfulfilling year at University, I quickly jumped at the opportunity to get back out on the road, soaking up experiences rather than reading about them in heavy textbooks.

sail captain

When we landed in the Caribbean something inside me clicked. I knew that if I found myself a job on another boat I could make a living spending my time outdoors. It was revolutionary to realize that I could make a living doing something that I loved.

At first I worked as a waitress and then found jobs working on charter boats in St John. I started with small part time positions and eventually worked my way up to being a full-time first mate on the most renowned boat on the island. After putting my time in, I earned my US Coast Guard 100GRT Masters License.

Since then I have gotten a job as first mate sailing across the Atlantic Ocean, spent a summer working in the Mediterranean, worked a whale watching season out in Hawaii and a summer season in Long Island, New York. I have also been able to take breaks to travel. In the past year I have made it through Thailand, the Philippines, China, Taiwan, Costa Rica, Canada and now Cuba.


Finding a career in sailing has given me so much freedom and it’s something that I want to encourage other people (especially women) to pursue. It’s not some exclusive world where only the most elite people can participate; it’s actually a viable career field for people who love adventure!

If you’re interested in learning more about how to find a job on a yacht check out my free guide here.

Liz Gilooly

This article was written by Liz Gilooly, a sailboat captain with a passion for travel. Through her career in sailing she has been able to travel all over the world. You can find out more on her blog – Moxie & Epoxy.

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