How to keep a working holiday lifestyle going long-term

We’ve been travelling for one and a half years now continously and we have learned a lot about how to do it, and have some advice for people looking to do the same thing. For the most part this is just like living, working and renting an apartment but in different countries and cities. Here’s how we do it.

Pick countries in the Shengen Area and then outside, rinse and repeat

The Shengen Area per Wikipedia is:

The Schengen Area ( /ˈʃɛŋən/, /ˈʃɛŋɡən/) is an area comprising 26 European states that have officially abolished passport and all other types of border control at their mutual borders. The area mostly functions as a single country for international travel purposes, with a common visa policy. The area is named after the Schengen Agreement. States in the Schengen Area have strengthened border controls with non-Schengen countries.

Basically what this means is you can plan travel to any of these countries (France, Spain, and Italy are some Shengen countries) for 90 days cumulative, but then you have to stay out of the region for 90 days consecutive. (This is true as of 19 Nov 2017, but please verify this on your own before you go because rules can change.) So when we plan where we are heading, usually 2-3 months in advance, we are always thinking Shengen.

So for example we started in three Shengen countries: Latvia, Estonia, then Belgium, then we went to the UK/Scotland for three months, then went to Spain for two months, Italy and then out of the Shengen area for Romania, and Bulgaria for two months. We haven’t had any issues yet, but these things you should have ready whenever you move countries:

  1. What are you going to see in the country you’re visiting
  2. Make sure to mention you are travelling on your savings so they know you won’t be a drain on the system
  3. Where are you headed next? The most important thing to a country is to know they don’t have to support you, and your next destination tells them you are moving on
  4. Have your bank balances ready to show, but we’ve yet to have to show this or go this far to prove our financial stability; as a family we have gotten very little scrutiny and mostly smiles and waves from immigration staff around Europe and UK
  5. Have the name and address and phone number ready for your accommodation, this also shows you are prepared and won’t be a drain on the system

I’ve mentioned money a lot here, and not being a drain on the system, so how do you pay for all this is a question we get a lot.

How do we pay for this?

I’d love to say we are making more than we are spending, but we aren’t. I find a lot of solace in the fact we have had so many incredible experiences! Here’s more on the actual details of what we’ve spent:

We started with about $30,000 NZD and have spent around $40,000 NZD in the past year and a half on things like:

  1. Apartment rent
  2. Food
  3. Transport
  4. Activities

Our working holiday was never meant for us to get rich in money, but rich in experience. The most important thing here is it’s hardest to get started, but pretty simple to keep it going once you shut down your old life (either for good or temporarily).

We’ve been working both of us part time along the way, making about $2000/mo (being careful to not work in countries like the UK/Scotland where they will tax your earnings, even if you aren’t a resident) so considering these earnings to balance the expense of travel, and we recently sold some assets so we can keep going without building up credit card debt (we always pay off the cards within three months, but usually same month.

Keep in mind the expenses we don’t have right now like power, gas, car maintenance, insurance, are taken up by travel insurance, plane flights and other transport incidentals. I even got two partial crowns replaced in Seville, Spain, but that was a great deal; lots of dental tourism in Spain because they are cheap and good.

Obviously a single person travelling alone, staying at hostels, and eating $2 slices of pizza is going to get a lot more bang for their buck, and someone travelling staying in the best hotels and eating at fine restaurants can spend 5-10 times more than we are. Pick your rate of burn.

We choose the countries we go to based on currency. For us we are earning New Zealand Dollars so staying a long time in the UK/Scotland doesn’t make financial sense for us which is why two of the four months we were in Scotland we spent doing a house-sit twice, rent-free. Scotland is beautiful, and the whisky is legendary. Don’t be afraid of countries that seem outside the norm like the Baltics and the Balkans. Some of our best experiences have been in these countries!

Always remember your kids are a wonderful ice-breaker in every country you visit. Pick countries you’d regret not seeing, and find things to like, as you always will.

Book apartments for reasonable rates

The best sites I’ve found for finding cheap apartments are:


About 40% of our apartments are booked through airbnb but the rest have been booked through vrbo and homeaway, which seem much more popular in Europe and UK.

Find apartments with lots of good ratings – that means the apartment is constantly in use and the owner is reliable. Sometimes people advertise their place on a site but then want you to pay them in cash directly, try to avoid doing this as you have no recourse if things go south. We made one exception to this in Budapest and won big, we had a Skype call with the owner and made payments to him via PayPal which meant we could cancel that payment from a credit card in a pinch.

Always ask for a “long term rate” as these aren’t always advertised. It’s like negotiating but it’s not offensive to ask this. If the person really wants you to stay, they will give you a deal, between $30/40 day is pretty average, many countries charge in Euros even if their country isn’t using the Euro, so keep this in mind before you book.

Some countries and cities require a “tourist tax” to be paid on arrival so make sure you have the proper currency before you arrive.

When you get to your apartment, always know there will be things missing. I wish I could give a list to every apartment for what they must have, always, but it’s interesting to see what things are valued in each country. Some places have coffee makers, some don’t. Some places have spatulas and frying pans, some don’t. Some have ovens, others not. You just never know but this is part of the fun, adjusting to these changing circumstances. No apartment should be without a wine/bottle opener or some sort of coffee maker. Absolute essentials!

For your first one you will want to set up your profile, use a photo without sunglasses and a good smile and link your Facebook account and even LinkedIn if you want, these things help an apartment owner trust you quickly; vital for doing this working holiday thing.

Local transport, aka buses and taxis

When your plane lands, make sure you have a plan for how to get to your apartment. We usually get cash at an atm when we arrive (between $300-500 equivalent for expenses we can’t pay via credit card, make sure it’s one that’s in the open and from a locally trusted or international bank, and I always let my bank convert the currency rate, not the machine, I think that bank is taking more of a cut if you let them do the conversion.

Local transfer services are the most expensive but also the most private way to get to your place, but we usually find a big taxi and pile in. We’ve even piled into tiny taxis, bags on our laps. Research beforehand what a good rate is, as it can vary a lot. It will be much harder for you to get scammed or charged much more if you know the going rate.

And don’t do what we did in Rome after arriving in the evening exhausted from Spain, which was to let a rogue driver take us to our apartment; he drove like a maniac and then demanded 10 extra euros higher than our agreed-upon price. I declined and I think he swore in Italian before leaving in a huff. It could have ended badly, so don’t make that mistake and let someone make this decision for you, no matter how persuasive they are.

And by all means figure out local transport while you are staying somewhere long term, some countries have excellent deals on travel cards that let you hop on a bus, train or tram all over the city. We are fond now of not having to drive anywhere, and Prague has probably the best transport system we’ve ever seen, we bought four transport cards for 30 Crowns each (about $15 NZD) which required only a current passport photo and passport verification.

My Prague 30-day travel pass
My Prague 30-day travel pass

How to handle money and currency exchange

You will find you are constantly converting local prices to your own currency, this is pretty simple once you find the rate on Google. I usually search “czech to nzd” to get the conversion for Korunas to NZ Dollar, then try to find an easy way to do it in my head.

As you move countries you will have money left over, but you can oftentimes exchange your notes for the local currency, just make sure you have enough to make it worthwhile. If you have less than a few dollars in value, don’t bother they won’t exchange that, or coins. So in the end it’s a delicate balance of getting enough cash and spending it before you leave rather than trying to hold onto it for later. The exception here is Euros if you know you’re going to return to the Shengen Area.

Ok I’m sure there’s more, please let me know your questions in the comments and I’ll make sure to answer it in a future blog post!

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Nathaniel Flick

American born, Kiwi made. Bass player, black coffee, dark beer. Travelling Europe till 2018.

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2 Replies to “How to keep a working holiday lifestyle going long-term”

  1. My question is this: have you bought me a souvenir in each country, and when are you going to deliver them?

    1. Ha ha zinst! Read this blog, lots of souvenirs in here. 🙂 Not sure when I’m back in the States but whenever I see you we are going to have a beer and a great catch up.

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