When you tell someone you’re going on holiday, nobody ever asks why. Unless you happen to be going on holiday alone, and then it’s almost always the first thing they’ll say. The words are usually accompanied by pitying eyes and a concerned tone of voice, because if you’re going away alone, the assumption is that something has gone terribly wrong. Like you’ve been dumped, lost your job, or entered into an existential crisis that can only be cured by a year of nomadic solo living (thank you, Eat, Pray, Love).
These reasons aside, why else would you dare to travel solo? Well, as someone who has been away on her own several times in the last few years, allow me to educate you. Because once you start travelling this way, trust me, you will want to do it again – and may begin to wonder why you ever travelled with anyone at all.
The first time was out of necessity: a long weekend in Paris I’d originally booked for me and my boyfriend. We broke up. I couldn’t get any money back on the trip. So I went alone. The first dinner was, admittedly, a little bit teary. But the following day, I was writing in a cafe when someone I went to school with randomly walked past.
We ended up having the most fun night out together that ended in a karaoke bar with a group of French students. That wouldn’t have happened had I not been on my own.
Since then, I’ve gone away a few times of my own volition: a week in Santorini, a few days in Provence, and a stint in Lisbon. Every time, I’ve come away feeling peaceful and restored. Much more so than when I’ve gone away with other people. Once you overcome the initial society-induced stigma, there’s something deeply satisfying about being on holiday alone.

There are no schedules to abide by, no dietary requirements dictating your choice of restaurant, and no idle chatter to engage in on the beach when you’d much rather be sunbathing and reading in silence.
As an anxious freelancer whose iPhone is practically glued to her right hand in case of a last-minute work opportunity, I’m someone who struggles to switch off. Going away alone is one of the only things that allows me to do just that. I can exercise, read, and sit in silence with my own thoughts, allowing my nervous system to fully decompress.
Currently, I’m single, which makes travelling alone more of a necessity, perhaps, than it would be if I were in a relationship. But I know I’d still want to go away on my own even if I had a partner – we all need time to ourselves. As an only child, I’m particularly reliant on it in a relationship. It’s the antithesis to what Jamie Oliver and his wife Jools would suggest – the couple has filmed an advertising campaign for the app Life360, which is designed for family members and couples to track one another’s locations. I can’t think of anything worse.
While there may be safety reasons behind using a tracking service, I feel like there is something odd about being so bound to your partner that you feel compelled to track their location 24/7. This is the kind of behaviour apps like this facilitate, whether intentionally or not. For me, it will always be important to have travel autonomy, regardless of whether or not I’m in a relationship.
While friends in relationships say they’d never “let” their partner go away on their own without them; it would feel like a rejection. I think going away alone is a healthy and necessary part of life. It’s a privilege if you can do it and can be empowering, too, as a single woman
If the thought of solo dining sends shivers down your spine, book a cabin or cottage so you get privacy, space to work on that book or creative project
Molly Cooper, co-founder of Curated Spaces
If I have one summer without a holiday alone, I start to get twitchy. This is the point I’m at as I write this. Except I cannot decide for the life of me where to go. That’s one catch about travelling alone: you have nobody to bounce ideas off of; the choices are entirely yours and yours alone. This is great, but also totally paralysing, particularly in my current, rather burnt-out, state, where making any kind of decision feels impossibly difficult. Do I go to Granada for a few days to double up on a research trip for a project? Do I find a seaside hotel somewhere in Italy? What about Greece? Isn’t Greece always great?
There are some limitations and personal preferences that make the choice easier: firstly, I cannot drive. So, like many solo travellers, I need somewhere that has everything I need within walking distance. Secondly, I’m more of a beach than a pool person. I don’t have children and would rather not hear or see other people’s while on holiday – sorry. That means an adult-only hotel is ideal. But I also don’t want to be surrounded by couples, which rules out a few overly romantic spots.
These are my parameters – where you want to go on your solo trip will depend on yours. “Be honest about what you’re looking for,” suggests Molly Cooper, co-founder of Curated Spaces, a travel booking platform and community based on personal recommendations. “If the thought of solo dining sends shivers down your spine, book a cabin or cottage so you get privacy, space to work on that book or creative project, and no awkward table-for-one moments.”
Alternatively, if you’re looking to make new friends, Cooper suggests booking a pub with rooms or a small guesthouse. “Somewhere small and family-run is ideal, because the owners will point you to the local spots you’d never find otherwise,” she adds. If you’re thinking of a hotel, try seeking one out that has a communal lounge, café, rooftop, coworking area or organised activities.

“This can give you the chance to meet people without being forced to socialise,” says LP Maurice, travel expert and backpacker. “The Social Hub in San Sebastián is a good example, as it blends private hotel rooms with co-working and communal spaces. If you are comfortable staying in hostels, they can also be a good option for solo travellers. Koba Hostel in San Sebastián is close to the beach and offers shared and private accommodation, while Impact Beach House in Estoril in Lisbon is near several beaches and provides women-only dorms and common areas.”
Those looking to travel alone but in groups should seek out companies like WeRoad and FlashPack, which offer tours tailored to solo travellers. I’ve done one to Mexico with WeRoad before, and it was brilliant. Then there’s Club Avandra, which is a private members travel club designed specifically for women who want to travel in small groups.
Prioritising ourselves and our own wellbeing in a work-obsessed, screen-addicted world is not something to be sneered at
For this particular trip, I want to be left alone. I always head to Mr and Mrs Smith, a booking platform featuring a carefully curated group of uniquely stunning properties, with good perks for regular users, too. My focus this time around is on unpretentious hotels near the beach in quiet places. Sicily looks appealing, as does Paros. I’m yet to book anything but have my eyes on a few that might fit the bill: watch this space.
I’m still not entirely sure where I’ll end up, but I’m making it a priority. And when someone tells me they’re going away alone, I make sure I never ask them why. Instead, I reply, “Well done.” Because prioritising ourselves and our own wellbeing in a work-obsessed, screen-addicted world is not something to be sneered at. It should be celebrated.