How to take the Leap to travel solo when you’re over 40

A little while ago Two’s a Crowd did a podcast on solo travel with Australia’s Queen of travel, Catriona Rowntree.

It was an awesome conversation all about solo travel, but what really struck me about that interview, and what has stayed with me were the words of one of our solo travellers who agreed to be interviewed by Catriona.

Natalie, who travelled with Two’s a Crowd to South America, said about taking the leap to solo travel “I realised it was time I pulled on my big girls’ pants…”

We can all relate to Nat’s sentiments, there are things we all say we’re going to do, someday. And for many people that one thing is travel.

These days, with the prevalence of social media it’s even harder to ignore the travel bug. We see family and friends leaving for amazing adventures, follow their photographic journeys through the highlights of far flung destinations and wish we too could be doing that.

And so many people will tell you it’s easy, just get out and see the world, “pull on those big girl pants, or older man’s slacks”, and just go.

But the reality is solo travel can be daunting. It can seem like the only people who travel on their own are aged in their early 20s, taking Instagram-worthy photos at every stop.

While it may seem like that, we’re here to tell you that’s actually not the case. There are millions of people around the travelling solo over the age of 40.

There are some definite advantages to hitting the road on your own: never having to compromise on where you want to go, deciding on your own itinerary, being able to travel at your own pace, not having to see that museum or famous icon just because it’s on your travel partner’s bucket list…

The thing is, when you’re travelling solo you can do just as you please and what’s not to love about that?

But if you’re struggling with actually making the leap, here are some things to consider that will have you booking a trip in no time.


<<Enjoy the experience of travel solo throughout the best places in the world with Two’s a crowd’s tours. More details here!>>


Start small

Travel doesn’t have to mean long flights, months on the road or overspending on your credit card. It can mean renting a house somewhere local, or travelling to a nearby country for just a few days. Many of our solo travellers start with a short trip not too far away, Cambodia perhaps, or Fiji. They get to see if they like travelling, what aspects of travel they like or don’t like and how they cope getting out of their comfort zone. In our experience, the majority of first-time travellers come back time and again, with us, on their own self-guided solo adventure, with friends they met on our tour, or a combination of all three.

The point is they made the leap, they booked that first trip and went.

Think about where you really want to

I can hear you yelling at me, well that’s obvious, but hear me out. As a solo traveller it’s really up to you where you want to go. You might have seen a photo years ago that you keep coming back to. Some place that you’ve always wanted to go to but have never been able to convince anyone else to come with you. Think about that place and imagine yourself there. How does that feel to you? It may look beautiful in a photograph, but the idea of actually being in that place may not be quite as appealing as you first thought.

Think too about how you like to travel. There is no point joining a walking tour if you hate walking or visiting Fiji if you hate the beach.

You can find more tips for finding a tour to suit you here.


Everyone will ask you whether an area is safe, particularly when you’re travelling alone. Do your research before you go. Read travel blogs and articles to find out what areas are safe and what areas you should avoid. You might be surprised once you start researching that places you never would have thought safe to travel to are actually some of the friendliest and safest in the world.

Wherever you go though, keep your wits about you Always know exactly where your valuables are and be aware of your surroundings.

Making friends on the road

As we get older it can get harder to make new friends, and travel is no different. But don’t be put off. Join a local cooking class or salsa class, interact with locals and other travellers in cities, ask questions, engage people. People are generally more relaxed and happier when travelling, it’s a great time to strike up a conversation to get advice on things to see or places to go.

And who knows? You might just make a new friend.

Think about joining a tour

Travelling with a tour group, like Two’s a Crowd, means you don’t have to do anything alone. On a tour you’ll find like minded people to chat to and to take that photo of you standing in front of your bucketlist item. You’ll have someone to share the adventure with and be able to pick up tips easily from other travellers for your next adventure.

However you choose to travel and wherever you decide to go, take the leap and go. We’re sure you won’t regret it.

Diane Squires is a writer and tour host with Two’s a Crowd.

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