The Pros and Cons of a Roving Retirement

Eight years into our roving retirement, my husband Tim and I sometimes still have to pinch ourselves to believe we’re living this incredible lifestyle. We’re currently riding bicycles across North America, meeting new people, seeing new sights and challenging ourselves every single day. I know that pedaling across a continent isn’t everyone’s cup of tea, but for us, we’re achieving yet another item on our bucket list. Many other roving retirees we’ve met along the way are achieving entirely different goals but are nevertheless creating the life that they want in their own unique style. The ability to move to a new location as the inclination takes us is one of the things we love about our life, but it’s not all ‘beer and skittles’, as they say. Here are five pros and cons of a roving retirement…and how we deal with the cons.


1. Getting to Know Each Destination.

Because we travel through countries and destinations quite slowly, stopping in one place for longer than those on the average holiday can, we get to explore more deeply and have time to forge connections and relationships with the locals. Returning to a favourite bar or restaurant a couple of days in a row, sets us apart from those who flit in and out of town and we find people open up quickly with advice, invites and opportunities.

2. We Move With the Weather.

We aren’t particularly fond of the cold, nor wet seasons in tropical climates. With a roving retirement, we can plan to be in places when the weather is at it’s optimum. Of course, we do get the occasional bout of bad weather but nothing like that if we stayed in one place all the time.

3. Avoiding Crowds and Cutting Costs.

Staying away from major tourist destinations in peak season has become an art form for us, saving us thousands, not to mention the stress. Who wants to line up in queues for popular attractions, pay top dollar for everything and jostle for space with busloads of school children? Not us, that’s for sure. And, back to point two, many popular destinations have far more pleasant weather in Spring and Autumn.

4. Freedom and Flexibilty.

Because we’re not tied to any one place, we can change our plans on a whim or incorporate new ideas and opportunities into future adventures. A chance meeting with a fellow Aussie in a street cafe in southern Turkey led to a 4-month sailing adventure in the Caribbean three years later. Next week we’ll cycle a couple of hundred kilometres out of our way to visit up with a good friend we met Ho Chi Minh City because her mum wants to meet us. We once stayed on in Africa for an extra two months because we got a deal that was too good to refuse.

5. Making Friends.

We’ve now got like-minded friends all over the world. Rather than just one social scene, we have connections with many. And when we do stay somewhere for a while, like when we base ourselves out of Ho Chi Minh City, Vietnam, we often have visits from those we’ve met along the way.


1. Saying Goodbye.

It can be hard to leave friends and family as you move on to the next destination, especially as you really don’t know when you’ll see someone again. But with social media, the ease of international travel and a realistic and flexible budget, we’re never really too far away. And let’s face it…just walking out your door and heading to the 9-to-5 grind can have its dangers.

We stay in touch on a regular basis with all of those who matter in our lives, along with new friends we make along the way. Frequent trips back to Australia are always a fantastic experience and while there’s always a few tears as we leave, most people are as excited and happy for our next adventure as we are and we go with no regrets. Our close family and friends know we’re there for them if needed and are just a phone call or message away.

2. We Don’t Have a “Home”.

Home is where the heart is…and our heart is on the road. We’ve done the big house in the suburbs with all the bells and whistles (and associated mortgage). When we sold our house and left Australia in 2010, some people worried that we were selling our long-term security. But compared to the freedom we have now, there’s no comparison. Australia, Broken Hill, Brisbane and Ho Chi Minh City are all home, if pressed. But we prefer to think of ourselves as world citizens.

We still have two smaller properties in Australia but they’re rented out and helping fund our travels. If we went home, we could stay in one of our townhouses until we decided where our next “home” would be.

We certainly don’t miss out on comfort. In fact, we’ve stayed in several million-dollar homes in the last two months (for free, thanks to housesitting). When we do stay for a while, for example in Ho Chi Minh City, it’s a cinch to find a new, fully furnished apartment (including linen and crockery) each time. On the road, we often housesit in luxury homes, enjoy character filled Airbnb’s and camp in the wilderness. Variety is the spice of life.

3. We Don’t Have a Lot of “Things”.

We don’t have a lot of stuff; not with us anyway. We do have some treasured possessions in storage back in Australia, but we sold most of our “things” before we left Australia in 2010. At the moment we have all our day-to-day possession in some panniers on our touring bicycles—around 20kg, in total! And even though that includes a tent, cooking and sleeping gear, we’ve probably still got too much. I can see a few more things being donated to the charity bin in the not too distant future because we’re just not using them. It’s incredible (and liberating) to find out how little you need to live a happy and fulfilled life.

4. It Can Get Tiring.

Even though we travel slowly, it can still get tiring, moving all the time. Taking time out from our journey is an essential part of keeping our energy and enthusiasm levels high. We intersperse longer trips with time in Ho Chi Minh City where we can regroup both ourselves and our budget in a place that’s still exciting and provides us with new experiences.

Extended housesits also allow us to rejuvenate. We appreciate the rest that these stints provide us with but it usually doesn’t take long until we are itching for the next adventure.

5. The Cost.

Being on the move usually costs more than staying in one location, especially if you’re moving fast. Transport costs impact on the budget and short-term accommodation is more expensive than extended stays. We reduce costs by housesitting, using Airbnb extensively and camping. We prefer to travel overland where possible and take budget airlines when we do fly.

Yes, there are some cons to a roving retirement, but to us, the benefits far outweigh the downside, and we’ve devised some foolproof ways of dealing with those. Eight years in and we’re not looking to settle down in one place again, anytime soon. If we have our way, we’ll be roving for many years to come.

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