Solo travel expert Catherine Leech shares the secrets to holidaying alone

Solo travel expert Catherine Leech shares the secrets to holidaying alone


Solo Travel Q&A with Catherine Leech

Booking that first trip away without the safety net of family or friends can feel like a big leap but, as prolific solo travellers will tell you, it could be the making of you and lead to memories you’ll treasure forever. One person who knows this better than most is Catherine Leech.

Co-founder of the travel website 101 Holidays, Catherine is a long-time pioneer of seeing the world solo. Since childhood, she’s had a keen interest in experiencing new cultures and fondly remembers her first time travelling alone at six years old to visit her grandparents in Portugal. Those early memories incited a passion in Catherine which saw her continue to hunt out new places before eventually compiling all of her knowledge, along with a few other esteemed travel writers, into the tell-all, know-all website 101 Holidays.

As Catherine and her co-founders are such believers in how stepping out of our comfort zones can enrich us all, they have even created a sub-website, 101 Singles, to dig deeper into that topic. At Flavours, we also know how important building confidence through doing this can be, which is why we design our holidays to cater to solo travellers and encourage meeting new people, in new places and learning new skills.

Here, Catherine – who is also a big advocate of group singles holidays and the benefits this can have – shares with us her memories, thoughts and advice on solo travel to inspire your next trip.

How did those first trips abroad with your grandparents inform your love of travel?

Caravan in a Lisbon caravan park

‘I’ve had a lot of practise at solo travelling because I started aged six! Yes, my grandparents moved to a caravan site in Lisbon and my mum packed off to visit them alone. I flew from London as an unaccompanied minor and absolutely loved it. You could say I’ve never looked back and actually, these memories have remained really special to me.

‘When I think back to those times, it’s about the smells and tastes for me. I vividly remember driving through Portugal, Spain and France with their caravan and joining local farmers on various camping stops en route. I remember riding on an ox-drawn plough, picking apricots and even milking goats. The smell of eucalyptus and pine needles, even now, always takes me back to those long hot summers in Europe. It ignited my love of food and gastronomy too – my grandparents always encouraged me to try all the fresh local produce. In fact, it was the only food on offer so I’m not sure I needed much encouragement.’

After many years solo travelling, what made you decide to start 101 Holidays?

Beautiful waterfall in the breathtaking Sri Lanka

‘In short, I had a lightbulb moment. It was while on a group yoga trip, in a yurt on a Turkish mountain with 22 strangers that I realised travel was the most important thing to me and I no longer wanted to do a traditional job. I immediately came back to London and quit my job to travel around Sri Lanka for two years.

‘Once back in the UK, I moved to southwest Dorset, where I still am, to get away from the city and enjoy a different lifestyle. This gave me the time to focus on 101 Holidays and start the project with two like-minded friends who had been writing travel for the Sunday Times for years. We felt that at that time there wasn’t enough online sharing brilliant travel inspiration and real experiences in one place. Between us we had the expertise so we broke it down in a way we felt at first made the most sense which was by month, the idea being that you know when your annual leave is, and we’ll tell you where to go.‘We’ve now got five sites, including 101 Singles Holidays. So, the business has grown and we have ideas for anyone, depending on what they’re looking for and when they want to go. It’s my baby, apart from my spaniel. And it keeps me out of mischief!’

What’s your advice for first-time solo travellers?

‘I think if you’re planning your first solo trip, make it something where you know you’re going to be amongst people who are a bit like you – who share an interest. And that doesn’t mean that you have enforced sociability, but simply that you have that companionship to dip in and out of as you want. And that doesn’t need to be a special interest small group holiday, but I think it helps. I think it’s a really good way to break the ice. I think for most people, once they’ve travelled solo once, it’s a real bug.’


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We agree! What has been your experience of a group solo holiday?

‘One of the richest experiences I’ve had was a 10-day yoga holiday in Thailand three months after the 2004 Tsunami. Our group of 20 (im)perfect strangers was able to generate income for people whose livelihoods had been utterly devastated, to listen to the stories of survivors and to forge powerful friendships in a very short period of time, some of which endure even now. Of course, we were all bound by the common thread of an interest in yoga – and that’s where a special interest holiday is such a fantastic idea for anyone travelling solo, from first-timers to seasoned travellers. A shared interest is the ultimate ice breaker.’

Let’s get specific – where would you advise a solo traveller to take their first trip in Europe?

A view of Lisbons horizon
‘That’s a tough one. It really does depend on what you are looking for but I think that Lisbon is hard to beat. It’s incredibly friendly, there’s lots to see, including a really vibrant old town, bustling markets and stunning waterfront plus the restaurants are superb with a very relaxed vibe. You can hop on a tram to go from district to district but it’s also a very walkable city and I love the fact that the beaches of Estoril and Cascais are a short train ride away.’

What about if we’re feeling a little braver, where’s a great long-haul destination as a solo traveller?

The stunning beachside in Cape Verde
‘I have had good experiences travelling solo in Thailand, Cambodia, Sri Lanka, Australia, Cape Verde and throughout the Caribbean (the latter generally with a work hat on). In all cases, it’s always important to tap in to local advice and news and, of course, to respect the cultural norms. But above all, to travel with an open and inquisitive mind.’

Do you think solo travel is becoming more common?

The town Malta at sunset

‘I remember going on a sort of grown-up holiday to a very grown-up hotel, Phoenicia, in Valletta in Malta in my 20s on my own. And that was really quite unusual then for people to go on a hotel holiday on their own. And I think in those days, if I’m frank, people would look rather pityingly at you as you were having dinner on your own and would often come over and say, “my dear, would you like to join us for dinner? You look terribly lonely”. That’s like a no, thank you. No, I’m really very, very happy.

I don’t think that happens so much now because I think it is so much more accepted that people actively choose to go on holiday on their own and are perfectly happy to sit and luxuriate in dinner or a cocktail or just read a book on the beach, whatever it is.’

What do you think puts people off solo travel?

‘It’s a really good question. And I think it’s changing all the time. But I think for most of us, if you’ve never travelled on your own before, there is just a sense of – my holiday time is very precious to me, this is costing me money, I don’t want it to be a disaster. I think there’s an element of that.

I think there used to be a nervousness about being labelled that, if you went on holiday on your own, you were somehow either some sort of veracious woman or it was all rather desperate or that you were going to go dating. Things have moved on tremendously now, but I think that people don’t feel that same level of fear, but sometimes it can be hard to find the right holiday for you and that then becomes the problem. And that’s where something like 101 Singles Holidays is a great way to find what you want. More importantly than that, if you have a particular interest, and this is where Flavours Holidays is such a great option, that you can enjoy your holiday, pursue your interests, but also be with likeminded people.’


What do you think the future of travel is?

‘I think the interest in solo travel will continue to increase. There are a lot of people who have been spending more time with their partners than they might have done before, to put it gently, and I think that there are people who have developed interests that they might have not had before. And I think that for an awful lot of us, we’ve become more aware of the importance of our downtime and our interests outside of work. I think it’s been quite transformative and it will feed into what people do with their leisure time.

‘We Brits, we have holiday-taking in our DNA. We view it as a virtual birth right to go on holiday! We might change how and where we travel, what we spend, but we will go on holiday. And I think a lot of people in relationships will want to spend time pursuing their own interest on a holiday that they might not have done, having not gone through all of this.

‘The key areas that people are looking for are celebration holidays – fiftieth birthdays, sixtieth birthdays, 25th wedding anniversaries, special events. I think these are going to take on an even bigger significance after all of this because we want to spoil ourselves. We want to mark the special events, I think we’ve all been rattled! And so, we’re certainly seeing a trend of people wanting to do more, do bigger, do better, for marking special events in their lives for next year.’

If you’re tempted to dip your toe in the solo travel pool, find out more about our group holidays with our latest brochure here.

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Flavours Blog

Food, Recipes, Lifestyle and Travel blog – by the Flavours Holidays team.