9 Ways to Take a Working Holiday (aka Never-Ending Vacation)

“If travelling was free, you’d never see me again.”

Hmmm… No.  I object.

I certainly appreciate the sentiment but it implies that you can’t travel without being rich.  It kindly lets you know that travelling is out of your reach and that is simply not true!

Rather, I say,

“If you knew how cheaply you can travel, you’d be travelling right now!”  

Given the job market, appallingly low wages in the U.S, and student debt, it’s understandable that we think we lack the money/ability to travel the world.  It feels daunting and as a result, we feel stuck wherever we are because we think we can’t to do what we want; that we can’t afford to travel.

I felt that way before I decided to leave home to travel Australia.  I was too afraid to leave my job for fear that I would be making a mistake.  How could I leave a comfortable job that paid me well, a job I felt fortunate to have, to risk it all and frivolously move to Australia?  Am I crazy?  Irresponsible?  What about retirement?  Oh, shush, Tommy.  Put all that nonsense away.

If you are in one of those situations, I’m here to tell ya: you do not need to be rich to travel (and it is not irresponsible).  All you need is a desire to travel and a bit of money to get you started.  You just need enough for a plane ticket and a few weeks accommodation.

The problem is not a lack of money, its a lack of knowledge; you just don’t know how to do it (yet)!  That’s alright, I didn’t know either…

Until one fine day I found out that you can WORK while you TRAVEL.

Mind. Blown.

My world changed.  I began to reimagine my 5-year plan.

It seems so simple but I didn’t know there are countries which have working visas available to Americans.  It just seemed like a vague possibility to work abroad.  Obviously other people have done it… But how do I do that?  There are a few ways:

  1. There are a few countries offering work & travel visas to Americans, and you can obtain these visas quite easily.
  2. There are spots in our own great nation – where we Americans already have the right to work – places where you only dream of vacationing – where you could be living in paradise!
  3. And finally, there are opportunities around the world which will allow you to travel for free (or almost free) for months on end.

Here are 9 ways to take a working holiday (aka never-ending vacation):

New Zealand

Americans 18 years old but not more than 30 years old can apply for a Working Holiday Scheme in New Zealand.  The visa will allow you to travel and work in New Zealand for up to 12 months, and you may also study for up to six months (bonus!).  From what I’ve heard, New Zealand is amazingly beautiful, I mean, just look at that breath-taking picture! (Shout-out and many thanks to my friend Gina who gave me the above picture of Mt. Cook and Lake Matheson to use for this article – brilliant!).  I’ve met a few Kiwis since I’ve been in Australia and I have to say they seem to be the most kind, humble people.  I cannot wait to go to New Zealand!  You could be living there!  For more information, go here.


Similar to New Zealand, Americans 18-30 years of age (but not yet 31) can apply for a Working Holiday visa (Subclass 462) in Australia.  After applying and receiving approval, you may stay for up to 12 months to live, work, and travel (you can study too, if that’s your thing).  Imagine working-to-travel in a cafe down one of Melbourne’s famous laneways, near the Sydney Harbour, or at a wildlife habitat amongst cockatoos, kangaroos, and koalas!  More information here.  My experience applying for this visa here.


Castles. Sheep. Rolling hills.  If you’re in college, or you just graduated from a post-secondary school in the last 12 months, you may be eligible to obtain a Working Holiday Visa in Ireland!  I love Ireland.  I’ve been lucky to visit twice and I definitely would have spent a year living and working there, if only I had known about this opportunity when I was eligible!  You could be pouring beers in Dublin or doing something cool in the Irish country-side (mowing the beautiful green grass on the rolling hills?  Idk, you decide!).  If you’re eligible, don’t miss out like I did.  More information here.

U.S. Virgin Islands

If I lived in the U.S. Virgin Islands, I would pretend I am Jack Sparrow, and I just washed up onshore to a beautiful, untouched island with a bottle of rum.  And treasure.  Actually, I will do that, except no rum because I hate rum.  Americans are able to work in the U.S. Virgin Islands (St. Croix, St. Thomas, and St. John) sans visa BECAUSE IT IS A PART OF OUR COUNTRY.  You don’t even need a passport to visit.  You could be living/vacationing/working in the Caribean all at the same time!  See you there – I’ll be daydreaming on the beach.


 I didn’t think about Guam too much until recently.  When I did think about Guam, my thoughts were like, “I wonder why people go to Guam?” and “didn’t I hear something about a guy in the rainforest who still thinks there’s a war going on?”  But now, after I met a Californian who was recruited to work at a resort in Guam, I see it as a beautiful Pacific island where Americans are legally allowed to work in paradise!  Due to its proximity to Asia, Guam is ideal as a jumping off point for travelers who want to save money before travelling to Asia, Australia, or New Zealand.  More info here.

Puerto Rico

Dear Puerto Rico,

I’m sorry I haven’t had a chance to visit you sooner but thank you so much for being a U.S. Territory.  When I do finally visit, the fact that I’m free to move in is a big plus.  You know, in case we fall in love.  I’ll help pay rent because I’ll be able to work.

Love, Tommy

Volunteer on the Peace Boat

When I heard about the Peace Boat, I thought “I need to get on that boat!”

A little background: “Peace Boat is a Japan-based international non-governmental and non-profit organization that works to promote peace, human rights, equal and sustainable development and respect for the environment….Peace Boat carries out its main activities through a chartered passenger ship that travels the world on peace voyages. The ship creates a neutral, mobile space and enables people to engage across borders in dialogue and mutual cooperation at sea, and in the ports that we visit.”

Anyone can apply to volunteer on the Peace Boat.  If you are a linguist or teacher this is a perfect opportunity.  You could be living on a boat travelling the world for free.  Here’s a link to their website.

Teach English abroad

Just Google “teach English abroad” and you will find heaps of opportunities to work in counties such as Thailand, Japan, China, and South Korea.  A friend of mine, Brittany, worked as a teacher in Seoul, South Korea and loved it!  Basically, here’s how it works: there are companies (recruiters) looking for Americans to place as teachers in various countries.  They lead you through the process and ultimately you are given a working visa to work as a teacher.  They value your English speaking skillz and your status as a native English speaker.  If backpacking is too unstructured for you, this is a great opportunity to get out of your box, work abroad in a structured position, and make good money.  This is also a brilliant opportunity if you don’t have money for a plane ticket, because the plane ticket is often provided.  Google away!

Work as crew on a boat

Boats don’t sail themselves!  I learned about this one from a girl I shared a room with in Port Douglas, Australia. When I introduced myself to her, she told me she had just been on a boat for six months.  Yes, six months.  How? Where?

She sailed between New Zealand, New Caledonia, Fiji, Australia, and other little islands.  I was like, “how in the world did you get to do that?!”  Then she told me about findacrew.net where boat captains and boat owners look for crew to help sail/operate boats in their boating adventures.  The rest of that night, I was literally gone, stuck in a daydream, searching the listings on the site and imagining all the amazing places I could see, (and only see), by working as crew on a boat.  Trips can last for days or months and occur all over the world.  All you have to do is take a position as crew.  Some opportunities require you to contribute a small amount of money for food (it varies by opportunity but I was told about $3 per day) and others actually pay you to work on the boat.  Find your boat here.

There are TONS of other opportunities out there like volunteering at an orphanage in another country.  Or you could move to Hawaii!  A friend of a friend of mine applied (and was accepted) to work on a farm in Hawaii where they practice yoga everyday and get to run around naked and farm.  There’s something for everyone in this vast world!

P.S.  Many of us worry about money.  If that’s you, don’t forget that money is not what makes a fulfilling life (its life experience, people, learning, and love!). There is more than enough money to go around and if you are doing what you love, you’ll be much more likely to find money along the way.  If you’re interested in travelling but are afraid to get out there, don’t think too much.  Just follow your heart.

2 thoughts on “9 Ways to Take a Working Holiday (aka Never-Ending Vacation)

  1. LauraB says:

    This is awesome! I’m going to share your blog with some relatives as they might be up for this. I’ve also heard that Guam is a great place and that Thailand (some place other than a city) is a beautiful experience.

    Liked by 1 person

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