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.

What Our Clients Say

20 out of 10!

The trip was just great - I can't really think of any negatives. Diane will back me up when I say I usually give 10/10s - I gave her 20/10. Trish, Canada/Alaska

Excellent trip

I found the overall trip excellent. I believe Diane's professionalism, inclusive personality and ability to relate to all contributed to this. She worked to ensure the group was cohesive without individuals impinging on the personal space of others etc. a good skill to have and one she applied effectively. Kate, Canada/Alaska

Fantastic value for money

Fantastic value for money paid. Russell our guide is an asset to your company... he was fantastic! Overall the trip was magical from start to finish. Well done Two's a Crowd ... the best trip ever. Barbara, Canada/Alaska

Fantastic first solo trip

I had a fantastic trip. Absolutely loved Canada and Alaska. It's the first time I have travelled solo and was pleasantly surprised to find a bunch of people that all got on so well. Diane our host was great. She did a good job of getting us altogether for meals, excursions, shopping trips etc. I liked that she quietly got things done without being loud or "in-your-face". She was good at being one of us as well as our leader. Wendy, Canada/Alaska

Good balance of activities and spare time

Had a great time. Good mixture of organised activities and spare time. Diane was an excellent tour host. Russell the tour guide was great, very knowledgeable and personable with his insights into growing up and living in Canada. Sharon, Canada/Alaska

Well organised trip with an excellent host

The trip was well organised, with a good mix of activity and free time. The scenery was spectacular and fellow travellers were a great bunch. Diane is a excellent host - helpful, courteous and above all a pleasure to know. I found her bubbly personality a bonus and can only speak highly of her. Gary, Canada/Alaska

I had a fabulous time

I had a fabulous time. Lake Louise and the hotel were magnificent. The cruise was excellent. Diane made sure that she was available for group meals and sightseeing, and was alway in good humour and great fun. I would recommend your company to everyone and am very interested in the Scandinavia  tour at the end of 2017.

Cathy, Adelaide - Canada/Alaska May 2016

Great holiday

What a great trip! I experienced so much and participated in all that was offered. I had read and reviewed as much as time allowed me but was not prepared for what the trip gave me and that is a better understanding of the beautiful people of both countries. - Lesley on Vietnam/Cambodia

In good company

I thought the suggestions for optional things to do, in the "free" time were very good. So good, we really ended up with very little free time. So much to do! - Mary on Vietnam

Great time together

I found the trip interesting and eye opening with a great overview of both Vietnam and Cambodia. The other travellers on the trip were fabulous and we had a great time together. - Anonymous on Vietnam/Cambodia

Fantastic first experience!

Extremely well organised with fabulous guides throughout - especially in Vietnam! First holiday with your company and certainly not the last. - Glenys on Vietnam

Great group to travel with

Having a small group meant that the days were more relaxed and flexible and I really felt spoilt and looked after. Melinda on Borneo

Thoroughly enjoyed Uganda

Thoroughly enjoyed my trip especially Uganda. There was so much variety of things to do on this trip. Jaros & Julius were great. Thought in Kenya the Maasai Mara were beautiful people, so easy to get along with. Judy

Can’t stop talking about my experience

I just feel so privileged to have shared with the Maasai the most awe-inspiring majestic sights and sounds of Africa. The fantastic memories will be with me forever. Maureen

Absolutely enjoyable

Gillian was a fantastic host. She was there for us from the moment we reached Hotel Troy. Heather on Africa

Best holiday I’ve been on!

One of the best holidays that I have been on - really well organised. I would never have travelled to Vietnam or Cambodia on my own. Bronwyn

Well organised

Fun, well organised and a really great group. Barbara on Vietnam/Cambodia

Great time together

I found the trip interesting and eye opening with a great overview of both Vietnam and Cambodia. The other travellers on the trip were fabulous and we had a great time together.

Great value

Well done. No complaints. Very pleased with this trip. Great value for my hard earned dollars! Really enjoyed the [Vietnam/Cambodia] tour. 

Fabulous rapport filled with much humour!

A great bunch of people & I can't believe how we all had such a fabulous rapport filled with much humour!!!

I couldn’t fault anything.

The (Uniworld River) cruise was great, I met up with some wonderful people who treated me like part of the family !
The ship & crew were fantastic & the excursions were very good, I couldn't fault anything. I'd recommend this cruise to anyone.  Peter

Informative and educational

The entire trip was one of the most enjoyable and exciting. Also so informative and educational. I was so pleased to make the trip. Wish I was over there in that magical place.  Marjorie


I’ve just returned from the wonderful Kimberley trip.  It was my first experience with Two’s a Crowd and I was delighted.  Kay

Opportunity to experience

I have had the opportunity to experience things I would never had done by myself.  Solo travellers is a fantastic concept and use of social media has been a great way to share and keep in touch with friends and family. Judi

I need not have worried

Being my first tour and a senior member, I admit I was apprehensive but I need not have worried. It was great and I was very well looked after.  Can’t wait to go to Kenya with Two’s a Crowd.  Maureen

Smooth and seamless

A memorable trip of a lifetime, a wish fulfilled.  A fascinating cultural country steeped in history which I found totally enthralling.  Two’s a Crowd service was smooth and seamless.  Pam

A wonderful experience

It was a wonderful experience visiting Cambodia and Vietnam and gave me a better understanding of these countries. I had a great time with new friends, we had a good bunch and Leonie was the perfect host. Eric

Value for money

Value for money and outstanding co-operation from your staff and tour operators. Joan

Safe and secure and totally looked after

An awesome adventure for my first time overseas alone.  Leonie was excellent and both guides were also fantastic.  At all times I felt safe and secure and totally looked after.  Melinda

Well done Two’s a Crowd.

Leonie was an excellent host, the ideal person. I never felt any pressure to  be involved in every activity so I could explore alone during free time. Having 2 or 3 nights in most places was great – you could rest up or party. Well done Two’s a Crowd. Jenny

A completely different experience

It was a nice surprise holiday, a completely different experience from all my other holidays. Thanks. Piroska

I’ve had at least 10 travel agents.

In my travelling life, I’ve had at least 10 travel agents.  Two’s a Crowd is the first one where I haven’t had to correct anything in my travel documents.   Piroska

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I really wanted to meet the people behind it

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Two’s a Crowd on the internet was definitely meant to be!

I’m really enthusiastic about the niche you are determined to cover in the market, and have the feeling stumbling on Two’s a Crowd on the internet was definitely meant to be.

I find them inspirational

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Thank you for providing a service for people like me

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Excellent throughout.

The entire 14 days ran so smoothly from Two's a Crowd booking my flights to  airport transfers and then the 12 days camping in the Kimberley. Excellent throughout. Congratulations. Marjorie

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