My Recent Experiences of Solo Travel (and how they compare to group travel)

by | Jan 31, 2022

In this post, Steve Dillon, founder of Other Way Round Travel shares some of his experiences from a recent solo travel trip.

Recently I decided to leave my home base of London, UK to work remotely in Latin America.

It’s part trip “recce” – I’ll be travelling Mexico, Brazil, Peru and Colombia – meeting with partners and getting things sorted for our OWR trips later this year.

But it’s also personal, exploring my own curiosities while sampling the whole “remote working” thing.

It’s actually been a while since I travelled “solo”.

I had a gap year in my early-20s, travelling alone through Asia, Australasia and North America. But since then most of my personal travel has been with friends and family (and of course, on OWR trips)

So, at the age of 40, I decided to dust off the old solo travel flip flops and test the waters again.

Currently I’m two weeks in – staying in a place called Playa del Carmen in Mexico – and it’s been fascinating to contrast and compare the experience with our group trips at OWR.

Here’s some of the main things that have struck me.


(a topic I feel extremely passionate about)

I think whether travelling as part of a group or travelling solo, most of us are looking to meet people along the way. It makes the travel experience infinitely more enjoyable.

When travelling solo, there’s so many other people doing the same thing that, in theory, it should be super easy to meet a bunch of lovely people to hang out with. And in a way, it is. There are so many meetups, facebook groups, whatsapp groups etc… that you can easily find plenty of others in the same boat.

But, in my experience, it’s all very transient.

Everyone has their own schedule. Their own interests.

You’ll go for dinner with a group of people one night, then never see them again.

You’ll strike up a conversation with people on a day-trip, then, at the end of the tour, you’ll go your separate ways.

You’ll meet someone you really connect with…then tomorrow they’re leaving for their next destination.

You’ll have so many surface level conversations – “where have you been?” “where are you travelling to next?” – but rarely ever get to know anyone on a deeper level.

In my two weeks so far I’ve easily met and chatted with over 30 people. And about three of those I would now genuinely consider to be solid friends, who I will keep in touch with going forward.

But honestly, the level of friendship I’m at now with those people is about the same as what I normally feel by Day 2 of an OWR group tour. 

Being consistently with the same group of people, day-in-day-out, with the same schedule and sharing the same experiences…it creates an environment where it’s just so easy to bond and forge deep connections. And that in turn makes the whole travel experience so much more fun.

Finding Your People

Then there’s the topic of finding, in the crowd, the people that you really click with. Those with similar interests and at the same stage of life. People you would genuinely hang out with in “real life”.

I think all of us during our travels have befriended people we normally wouldn’t. I know I have. And in a way that’s great. It opens your mind to different people and life experiences that you wouldn’t normally have insight to. That’s actually one of the greatest things about travel.

However – while there are more and more people in their 30s and 40s solo travelling – it is still predominantly a young folk’s game. 

20-somethings working on their best instagram poses. Where the social life heavily revolves around going to bars and clubbing.

And while I’m definitely not beyond the odd drunken night out… I generally don’t want to spend my days hungover and feeling bad while on holiday. I much prefer to get up fresh, and enjoy being in a new and interesting place.

And so, while like-minded solo travellers definitely exist, they’re just harder to find.

So again, if I compare that with one of our OWR trips, for me, it’s night and day. On group trips you’re instantly immersed with a group of people that come with that same mindset. It then becomes super easy to meet people whom you can genuinely connect with.


There’s no doubt about it. 

The single easiest way to meet new people while travelling alone – even with all the new modern tech – is to go to stay in a hostel.

And I don’t know about you, but, at the age of 40, I have no interest at all in staying in a hostel.

Granted, these days hostels are a lot slicker and you can even book private rooms. But, at the end of the day, a hostel is still a hostel (even if it has a fancy name like “co-living”).

So, it is a bit of a dilemma that I know most solo travellers my age face. Do you stay at an Airbnb or hotel and risk not meeting anyone? Or do you suck it up and just stay in that hostel? That’s kind of the choice you face.

For me the best compromise is to stay at an Airbnb while still dipping into the social events happening at the hostel. That’s what I’m currently doing here in Mexico. But, I’m not going to lie, you do feel a little bit like an outsider joining someone else’s party.

And again, if I had to contrast this with a group trip, you’ve already got the best of both worlds there. Great accommodation, with a ready-made social group to tap into.

Restaurants / Bars / Experiences

These days there’s an endless array of travel information available – the best tours to take, where to eat, where to drink, things to do etc…

You can check Google reviews, blog posts, Youtube videos, ask your hotel, your tour guide etc…and no doubt you’ll be spoiled for choice.

However, in my experience, even with the abundance of recommendations on offer, it is still very much hit and miss. You’ll find some brilliant little gems along the way, but, will still end up in lots of not so great places where you wish you hadn’t wasted your time.

(like when you ask your Mexican tour guide the best place to eat and he sends you to an Italian restaurant)!

There’s simply no substitute for knowing someone – someone with a similar taste to you – who either lives in that place or at least knows it inside out. They will take you to the places that 99% of tourists will never go (think about where you take your friends when they come visit).

And again, not to be hyping up our group trips too much (although I fear that ship may have already sailed), but that’s exactly what we do. 

We know where the locals go in the destinations we visit. I, personally, have tested all of the experiences and weeded out the bad ones (and believe me, there’s a lot). That way when it comes to running our trips, it all just works. That’s why our guests consistently love the experience. 

I think that this point can genuinely be the difference between an average trip and an exceptional, life-changing, experience..

Hassle Factor

Turning up at the airport and not really knowing how to get to the hotel (yep, I’m talking about me on this occasion).

Walking with your luggage to the bus station.

Buying a local sim so you can use Google maps. 

Getting lost. Splitting the bill between large groups. Trying to get by on minimal Spanish.

In a way, these are all part of the travel experience and do tend to make for funny stories. And I think that for longer term travel, it is good for you to learn to work these things out by yourself. It helps build confidence and resilience.

But there’s no getting away from the fact that these things are a pain. And they do tend to suck your energy.

So when you’re travelling for a short holiday/vacation it’s sometimes much better to just have all of this taken care of so you can relax and simply enjoy the trip.

(and yes, you guessed it, on a group trip this stuff is all just sorted for you)

In Conclusion

If you’ve read this far, I think it’ll be obvious to you that I’m a bit of a champion of group trips (hey, it’s why I started the company).

For extended travel, I definitely see the value in going solo. It really does push you out of your comfort zone and you’ll be forced to do things you would never otherwise do. It’s a fantastic growth opportunity if that’s what you’re looking for (not to mention it’ll just be cheaper).

But, if you’re simply going on a holiday/vacation and travelling alone, for me a group trip is a no brainer.

You’ll rock up to a ready-made group of friends, it’s completely hassle free, and you’ll get way more of an insider experience.

Honestly, I don’t know why more people don’t do it.

I, personally, was already a group travel advocate before I came on this current trip, but, this experience has massively re-iterated to me the value of what we do here at OWR (i.e. bringing together awesome groups of people looking to share the travel experience together).

I’m therefore super excited to go on our next trip.

I’d love to hear your thoughts and experiences.