Long term travel guide for couples — how to plan, fund and survive an extended trip of 3 to 12 months. Street Eats and Window Seats shares honest advice on slow travel, budget management, accommodation, visas and staying connected for midlife couples planning their big adventure.
The Now or Never Trip
Two Australians. Five continents. Twelve months. No return ticket. In late 2027 we’re trading annual leave for a year without an end date — and we’re taking you with us. Follow along at Street Eats & Window Seats.
Realistic Long-Term Travel: Some trips you just have to take
There are holidays, and then there are the trips that change everything. In late 2027, Mark and Bec are leaving their 9-to-5 jobs behind for twelve months to travel the world — properly, without a return ticket sitting in the back of their minds.
Five continents. Countries we've dreamed about for years. Experiences that don't fit inside two weeks of annual leave. This is the trip that's been quietly living on our bucket list since we came home from our last big adventure — and we've finally decided to stop waiting for the perfect time, because there isn't one.
We're calling it The Now or Never Trip — because at this point in our lives, if not now, when?
14 months, 19 countries, two kids pulled out of school
The Now or Never Trip isn't our first rodeo. Back in 2019, we quit our jobs, pulled our two tween daughters out of school, and spent 14 months travelling Europe and Asia. Nineteen countries. Countless memories. A few disasters. And an experience that changed how our whole family sees the world.
It was a leap of faith — no jobs to come back to, no classroom waiting. Just the four of us figuring it out as we went. We came home knowing we'd do it again one day. That day is 2027. Read more about us and how we got here.
🐘 Elephant Nature Park
Spending time with rescued elephants in Thailand — one of the most humbling experiences of the entire trip.
🧱 The Great Wall of China
Standing on the Great Wall with the girls. One of those moments where everyone goes quiet and just takes it in.
🚢 The Mekong River
An overnight slow boat down the Mekong River — two days of watching life on the river pass by at a beautiful pace.
❄️ Christmas in Poland
Spending Christmas in the snow in Poland with friends. The girls' faces when they woke up to a white Christmas morning.
Five continents in twelve months
The 2027 itinerary is still taking shape, but the ambition is clear — five continents, countries we've never visited, and a few old favourites we can't resist returning to. Here's what we're planning so far.
Africa
The continent we've never visited and the one we're most excited about. Safari, incredible landscapes, and food and culture unlike anything we've experienced before.
South America
From the Amazon to Patagonia, Machu Picchu to Buenos Aires — South America has been on our list for years and 2027 is finally the year.
Asia
Asia is where our hearts live. We'll be back — exploring countries we've not yet visited and returning to a few favourites we can never get enough of.
Europe
A continent with endless depth. More countries to tick off, more food to discover, and more cobblestone streets to get wonderfully lost on.
North America
Road trips, national parks, incredible cities — and more street food than we could possibly eat. North America on our own terms, with no schedule to rush us.
Middle East
Ancient history, extraordinary architecture, and some of the best food on the planet. The Middle East is a region that's long overdue a proper exploration.
Funding a Career Break: How two 9-to-5 workers fund a year of travel
The biggest question we get asked is always the same — how do you afford it? And the honest answer is: it takes planning, patience, and understanding the leave entitlements that most Australians don't fully use.
The Now or Never Trip is being funded through a combination of long service leave, accumulated holiday pay, savings, and bank interest that we've been quietly putting in place for years.
"We're not wealthy. We're not retired. We're just two people who decided to treat long term travel as a serious financial goal — the same way other people save for a house renovation."
Long service leave in particular is one of Australia's most underused entitlements. After years of continuous employment, Mark is entitled to take long service leave at half pay — which covers the base cost of being away for a year without touching savings. Combined with accumulated holiday pay, bank interest, and a spending fund we've been building, the trip is genuinely achievable.
Long Service Leave
Taking long service leave at half pay means a regular income continues throughout the trip without touching a single dollar of savings.
Accumulated Holiday Pay
Years of built-up annual leave paid out at the start of the trip, providing a solid financial buffer before we even leave home.
Bank Account Interest
With the right savings account, our nest egg generates solid monthly interest — covering a significant portion of day-to-day costs while we travel.
Dedicated Travel Fund
A separate spending account set aside specifically for experiences, flights between regions, and the unexpected costs that long term travel always brings.
What we've learned about planning long term travel
Based on doing this once before and planning to do it again, here are the things that actually matter when you're preparing for a year away.
Understand your leave entitlements
Most Australians don't realise how much long service leave they've accumulated — or that it can be taken at half pay, doubling the time off. Talk to your HR department and know exactly what you're entitled to before you start planning.
Start a dedicated travel savings account
Keep your travel fund completely separate from your everyday finances. A high-interest savings account means your money is also working for you while you build it — the interest alone can cover a meaningful portion of your monthly travel costs.
Plan regions, not a rigid itinerary
Book your big inter-continental flights well in advance to lock in good prices, but leave the day-to-day itinerary flexible. Long term travel rewards spontaneity — some of the best experiences happen when you don't have a plan.
Think about home base logistics early
What happens to your house, car, mail and subscriptions while you're gone? Planning the home logistics — whether renting out your property or having someone house-sit — is as important as planning the trip itself.
Get the right travel insurance
Standard travel insurance isn't designed for long term trips. You need a policy specifically built for extended travel that covers medical, cancellations, and gear for the full duration of your trip.
Have the honest money conversation
As a couple, get completely aligned on your daily budget before you go. Disagreements about spending on the road are one of the biggest causes of travel tension — knowing your numbers upfront makes everything smoother.