Vagabonding Case Study: Luke Armstrong

Luke Kenya

Luke Armstrong

Age: 28

Hometown: Kalispel, Montana

Quote: “Instead of living in a specific place in the world, you simply live in the world. Everywhere is your home and everyone is your neighbor.

How did you find out about Vagabonding, and how did you find it useful before and during the trip?

In 2011 I did a book review of “Marco Polo Didn’t Go There” and interviewed Rolf
Potts (
During my research for the piece, I found out about Vagabonding. I found it
informative not of a specific trip, but a certain lifestyle. The word vagabond, is
often used negative. For many people it sits on the same linguistic shelf as
“hobo” or “homeless.” Vagabonding instilled in me the realization that extended
overseas travel was not just possible as a lifestyle, but that if I was honest with
myself, this was a lifestyle that I could adopt. At the time I had traveled a bit, and
was living abroad. T this helped me in a decision I made in 2012 to become a
full-time location independent professional, AKA, a vagabond.

How long were you on the road?

While I have my “bases” in New York,
Guatemala and Kenya, I have been on the road for the last two years.

Where did you go?

Cuba, Canada, Kenya, Uganda, Morocco, All across the
USA, Mexico, Guatemala, Belize, El Salvador, Nicaragua, Panama, Costa Rica,
Honduras Chile, Peru, Colombia, Argentina, France, England, Czech, The
Netherlands, Iceland, Spain,

What was your job or source of travel funding for this journey?

Over these last two years, it has been playing music and writing–travel writing, publishing
books of poetry, publishing a travel anthology, and doing freelance marketing. I
also spent 5 months teaching at an NGO afterschool program in the Bronx, NYC.

Did you work or volunteer on the road?

I spent my last semester abroad in
Chile in 2007. After that I ditched my flight home and started hitchhiking Chile in
to Alaska. I volunteered in several NGOs along the way. In one of these
organization in Guatemala, Nuestros Ahijados, I was offered a director position
when the program director abruptly quit. I accepted and stayed for four years
managing 100s of employees and volunteers, and supporting a thousand
dependents. The highlight of this work came when I opened a malnourished
infant center in 2008, which was later featured on ABC 20/20 (https://

Of all the places you visited, which was your favorite? Cuba

Was there a place that was your least favorite, or most disappointing, or most

Though this seems contradictory, this was also Cuba. I went to
Cuba for closure. My grandmother was a poet like myself, and a very important
person in my life. She opened the world of literature to me when on my 13th
birthday she gave me a copy of Hemingway’s The Old Man and the Sea. This
caused me to have both an interest in Hemingway and Cuba, just as Hemingway
had had an interest and love for Cuba.

In December I had a plane ticket to visit my grandmother. She was not doing
well. She past away a few days before my plane departed. I showed up in time
for her funeral. Her funeral gave me no closure. So I loaded up a bag of her
poetry books, and departed for Cuba. She was a world traveler herself and had
already wanted to go. In Havana I did the opposite of shoplifting: I smuggled my
grandmother’s poetry books onto their shelves. In each I wrote, “To Cuba with
love, from Patricia Mees Armstrong, via her grandson.

Which travel gear proved to be most useful? A ScotteVest

Least useful? Nothing comes to mind.

What are the rewards of the vagabonding lifestyle?

Instead of living in a specific place in the world, you simply live in the world. Everywhere is your home
and everyone is your neighbor.

What are the challenges and sacrifices of the vagabonding lifestyle?

There are of course, financial concerns, since writing and music are struggles to earn a
living from at this stage in my career.
When you are always arriving somewhere new, you are also always leaving a
place. You are constantly saying goodbye to people and places that you love.

How did your personal definition of “vagabonding” develop over the
course of the trip?

Being able to call myself a vagabond and feel that it had a
positive, not a negative connotation.

Any advice or tips for someone hoping to embark on a similar adventure?

If you are wondering if you should do it, you have already answered that question:
you should. If you are wondering how you will pay for it, trust that openess mixed
with the tenacity of not giving up will lead you to find your balance.

When and where do you think you’ll take your next long-term adventure?

I went to Guatemala on March, 17th. This is one of my bases, so I will be
staying for two months. Then I will be traveling to every country in Central
America again. This fall I will be traveling to Asia.


Are you a Vagabonding reader planning, in the middle of, or returning from a journey? Would you like your travel blog or website to be featured on Vagabonding Case Studies? If so, drop us a line at and tell us a little about yourself.

Posted by | Comments Off on Vagabonding Case Study: Luke Armstrong  | April 18, 2014
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