I’ve become a well-practised single traveller over the last eleven years of singledom. To be honest, I was pretty good at it before then: jumping on planes alone to join a husband frequently working abroad for long periods of time; driving from Twickenham to Amsterdam over the period of a couple of years with my children during half-terms and holidays to join their dad. Going back even further, I just grew up with the idea that it was OK to travel alone, eat in restaurants alone, and for me it’s never really threatened any great challenge. It’s just what I do. But for the unpractised it can be quite daunting. And even for me, it’s not quite the same thing doing it through a different kind of necessity now rather than an occasional choice. Well, it is still a choice. But group holidays have never appealed; I’m not that kind of person, heading off with a group of unknowns, although I know lots of other people love it. I’m lucky to holiday often with good friends and my family, but sometimes if I want to get away for a break or go somewhere in particular, then alone is the only option. And there is an appeal to it; there are plenty of pluses even if inevitably some minuses.

Holidaying with others isn’t always all it’s cracked up to be. Even with your nearest and dearest, tensions can arise but holidaying with someone you’re not used to spending 24/7 with can be a disaster. We all invest a lot of expectations in our holidays: we reach mentally for the rarely attainable perfection – I’ve invariably found that even the best holidays have at least one day of imperfection when things don’t go quite so well – and it’s hard to let go of your own way of holidaying. I was talking with my lovely friend Annie the other day about trying to have another break away together some time next year and she remarked that we ‘holiday well’ together. Basically, if you go away with someone you need them to have pretty much the same idea about how to holiday. It’s no good going to a hot and sunny place with someone who hates heat; it’s no good going away with someone who wants to crash on a beach for two weeks and do nothing else if that’s not your style. If you like visiting archaeological sites and art galleries you’ll find a companion who hates that will spoil your own pleasure. And, of course, if like me you just love seeking out good food – restaurants, markets, food shops etc. – then someone who has no interest in food will be a poor holiday mate.

My son and daughter inevitably followed the backpacking trail during gap years and set off alone; well, Nicola travelled round China, Laos, Vietnam and Thailand with a small organised group and Jonathan travelled alone in New Zealand but had my cousin on South Island and a family friend on North Island to act as bases for him to return to during his travels. I’ve never really been a backpacking girl. I’m not a tent girl. I’m not a camper girl. No one has yet got me on RyanAir plane. Yes, I like my luxury. But not necessarily super luxury – I don’t usually stay in luxury hotels or apartments – but I do like a proper bed, hot running water and electricity. I did quite a bit of youth hosteling in my youth but nowadays I wouldn’t go near a dormitory; I like a room to myself or shared only with a good friend or family. What I’m getting at here is that I’m of an age where I’m not afraid to say what I like. I’m of an age where I don’t have to prove anything – well, holiday-wise anyway; just as I know what I like I’m also happy to admit to what I don’t like: that you’ll never get me trekking through a jungle or holidaying somewhere it’s minus 40. My years of single travelling have given me an insight into what makes the experience work well for me; I understand my needs better and know what I need to do to take as much of the potential stress out of the trip as possible. Like anyone else, when I go away I want to have a good time; I want to relax and have fun. So here are some of the ways I’ve learnt to give myself the best possible chance of doing that:

1. It’s an open road: Embrace the freedom to go exactly where YOU want, in the way you want

Your holiday destination is no compromise; or at least, not with another person. I have some self-imposed limitations: I don’t want to go anywhere possibly dangerous for a woman alone; I don’t want to go anywhere that requires vaccinations (I don’t do jabs of any kind); I have a limited budget so have to consider costs. I used to talk about travelling the world one day (partly because I thought that’s what exciting people did) but I’ve come to accept that my holiday comfort zone is pretty much Europe. If the right person said, Come to Asia, Come to Australia, Come to South America, then I’m sure I would go. But I’m a true Europhile; I’m a happy European. I’ve been to Italy so many times yet always love to go back and discover more of it as well as visit favourite places; I can’t imagine not ever going to Paris or Amsterdam or Venice again. My choices now are often governed by food – going to Bologna earlier this year, for instance – and why I’m determined to get to Turin soon. But art will draw me too: like my trip to Aix en Provence last summer or seeing Guernica in Madrid. The beauty of the light, the promise of sun (though unfortunately not entirely realised!) and the friendliness of the Greeks drew me to Crete last month. The bonus for the single traveller is that you can just sit down with a map and think, Yes, this is where I want to go!

 

2. Time alone – how long is long enough?

When you travel alone you come to know yourself well. There have been times when I’ve felt really proud of myself for some of my lone ventures but I’ve also come to understand my needs better; what I can cope with easily and what will be too much of a challenge. So, as I said above, I don’t feel the need to prove anything so I’m happy to admit that a week on my own on holiday is my limit. I’m really happy on my own for that long (though more frequently I make shorter, weekend-length trips), but two weeks with just my iPhone for guaranteed company would be too much. I know people who think they couldn’t manage that long; I know others who’ve happily gone off for much longer alone. It’s personal. Don’t give yourself unnecessary grief. If you’re not used to holidaying alone, go for short breaks at first. When you feel ready to move on, try just a week. Then maybe you might feel up to longer. But be kind to yourself; don’t give yourself unnecessary stress to outstaying your own single welcome.

 

3. Small friendly hotels and other places to stay

I’ve never been a fan of large and impersonal hotels but when travelling alone, staying in a small, independent hotel can make all the difference. Regular readers will know that my very favourite hotel is Hotel Al Ponte Mocenigo in Venice, where I’ve stayed many times. I’ve first stayed there on my own in 2006 but have since returned many times: with my children, with Annie and again on my own. Owners Walter and Sandro are always so welcoming; they will talk to me in the morning when I come through for breakfast, whenever I come in from a morning or afternoon out; they’ll ask where I’ve been, what I’ve seen and make suggestions. Now they ask me about my family too, since they know them. It makes all the difference and I value it so much. I found similar kindness and friendliness at Hotel Porta San Mamolo in Bologna earlier this year. While in Crete a couple of weeks ago, I chose to stay in a ground-floor apartment that gave me the opportunity to talk to neighbours and passing people rather than move to a quieter apartment with a better view. When you’re on your own, you have to factor in finding company for some of the time.

 

4. Reach out to others

Well, you might be lucky enough to come across someone to befriend, of course, but the chances are you’ll just be on your own – just as you planned. But I like to do a bit of reaching out. I invariably return to a favourite cafe or restaurant a few times so they get to know me. In Crete recently, I ate lunch or dinner so often at Meraki, just below my apartment, they started to talk to me more, ask me about my day, welcome me when I arrived as almost an old friend; they were wonderfully friendly and it really enhanced my stay. I find on my own that I end up talking to people in all kinds of situations and places much more than I’ve ever done before. That’s partly, I know, because I’m a much more confident and outgoing person than I was eleven years ago, but even so, I think being on your own attracts others to reach out to you. I just love this aspect of holidaying alone and have gained so much from it.

 

5. Engage with social media

I’m a social media junkie. My son bought me a Twitter mug; his own little joke with me about my Twitter addiction – he doesn’t have an account. I engage with Facebook, Twitter, LinkedIn, not to mention my email account, WhatsApp and iMessage frequently throughout the day. On holiday alone, it has to be said, it’s a kind of lifeline: I’m never really alone. Vodafone have made it all the easier for me with their EuroTraveller deal: £3 a day for being able to use your phone (calls – including to home and in country you’re visiting – and internet access) just as you would at home. My iPhone itself has become a holiday essential and has saved me when lost a few times: Where am I? I ask it – and it tells me!! It is nice to share and if there’s no one at your side to say, What a beautiful view!, What a fantastic meal!, then you can share via your phone and get a response. I’ll post on Facebook or Twitter, if appropriate, but often it’s a message to my lovely daughter who is great at keeping in touch with me while I’m away, and ‘A’ has been great at emailing a lot while I’m away. Getting a response from my son or brother is a little more tricky but in general, when you’re on your own there’s nothing wrong with using social media if you want to connect back home some of the time. Many people want to cut themselves off from home while away; I like to have contact. It’s up to you – what do you want?

 

6. Safety rules

I don’t mean a list of ‘rules’ but safety reigns supreme: play safe. At home, when I’ve been out in the evening and am coming home late at night, the walk from the bus stop into the back streets can be a little unsettling on my own if there’s no one else around, so I don’t talk into my phone, and I’m attentive. I’m used to it so it would be too much to say I’m scared; I’m not, but I am attentive. Because attentive makes sense. On holiday in an unfamiliar place, it just makes no sense to take risks by going down dark alleys on your own at night. For that reason, I tend to stay close to my hotel or apartment when it comes to eating out in the evening – or be prepared to pay for a cab. But I’m careful in other ways. It hasn’t been a conscious thing but I’ve become aware I’m more careful of myself when I’m doing something like clambering across rocks or swimming out to sea. I like a glass of wine with my evening meal; maybe a chilled small beer at lunchtime, but I never drink much: drunk and alone do not go together well. If there’s no one to watch out for you – watch out for yourself! The other thing I do is make sure my family have all my details: I email my flight numbers and times; my address while away and a contact number for either the hotel or owner of an apartment. For me, this isn’t an opportunity to go AWOL; I prefer people know where I am.

 

7. Some planning makes sense ..

I’m generally a very organised person, but I’m not a great planner when it comes to holidays. I like to take things as much as I can day by day. It’s not unknown for me to open my guide book for the first time on the flight out. But some planning makes sense. I do buy a guide book and for short trips, I’ve become a devotee of Lonely Planet’s Encounter series which focuses on separate cities, so I now have copies for Istanbul, Amsterdam, Rome and Venice. I print off relevant Google maps before I go: how to find my hotel from the railway station; how to find my apartment from Heraklion airport in Crete last month. I buy a phrase book and always look to make sure there’s a food section so I’ll understand menus! I’ll generally have in mind a couple of particular things I want to do: places I want to visit; things I want to see. I buy foreign currency before I travel to get the best rate. But I don’t like to have my time totally mapped out and often I find, just going with the flow works really well. Sometimes if you’re too focused on the plan, you miss lots of things you’d notice if you just wandered (see more in this post in Crete). The other thing I like to do is take books about the place I’m holidaying in: both non-fiction and fiction, so I’ll get those organised before I go.

 

8. Gently does it … be kind to yourself

A holiday is supposed to be … well, a holiday: recharging the mind and body batteries, relaxing, having fun … a break from stress (unless you’re into danger sports). When you’re on your own, this is particularly important. If things go wrong, there’s no one to share the stress; no one to take over. It’s all down to you. So make things just as easy as you can. I’m willing (and fortunately able) to pay a little more for a few cushion comforts when I go away. Thus, when I flew out to Crete very early in the morning – too early to catch a train to Gatwick – I paid quite a bit more than I would have done for a minicab to take me there, to stay in the Gatwick Sofitel. It gained me a couple of extra hours in bed … and with the long journey ahead and a lone one-hour drive from Heraklion airport to my holiday apartment along Greek roads, being the least tired I could manage seemed like a good plan. Even when staying in an apartment, I rarely cook or even have coffee there. I like to get out. Whereas when I went to France with my family a couple of years ago we often cooked ourselves in the evening; bought food in the markets and boulangeries to take home for lunch; made a big pot of coffee for breakfast in the morning and got croissants from the local bakery to bring back. I don’t push myself to do anything I’m not comfortable with if there’s a choice; and even if it’s something I planned to do before I arrived. I’ll treat myself to little things when I can and do my best to make sure I have a good holiday.

Do you ever travel alone? What’s your best tip for the single traveller?