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The sky’s the limit: ‘The world is large and holidays are short.’
The sky’s the limit: ‘The world is large and holidays are short.’ Photograph: Steve Parsons/PA
The sky’s the limit: ‘The world is large and holidays are short.’ Photograph: Steve Parsons/PA

Why is it so hard to book a holiday?

This article is more than 2 months old
Eva Wiseman

I’m tempted by the ‘Ultimate Mystery Holiday’, if only so I don’t have to make the final decision…

Once again summer is here and I have forgotten to book a holiday. I don’t know how you lot do it, with your diaries and your dates, and your savings, and your organising the cat, and your knowing what you want, before you want it. It’s not that I don’t want it enough. I want it more than enough. My internal holiday clock begins ticking in the barren dead of winter, a fantasy of beaches and freshly caught fish, but as the clock continues, the rest of me remains static, frozen in indecision and lack of imagination.

This, I realise now, must be when the rest of you are booking your time off work, scrolling your houses to rent near the sea, negotiating which group of your friends you can live with for a week without upturning the table of ancient relationships, negotiating which of your friends’ children you can live with for a week without… best not say. Good for you. Good for you.

As I scrabble around now for somewhere to take my family during the school holidays, I find myself drawn time and again to something online called the Ultimate Mystery Holiday. Perhaps you have seen it, have similarly heard its quiet knock on your pre-sleep dreams, have opened the door just a crack, only to find its mysteries haunting your waking dreams, too. The Ultimate Mystery Holiday is an option on a popular voucher site where, alongside the compost bins and cream teas, you can buy “an Ultimate Mystery Getaway from £99pp.”

It goes on, “Holidays include Bali, Mexico, New York, the Dominican Republic, Iceland, Italy, Egypt & More!” The first time I saw this online I assumed, with my typical worldweary cynicism borne of a lifetime of errors, that if I were to buy a voucher, I would, knowing me, end up holidaying for a fortnight at the little-known resort “& More”. But I kept finding myself back on the website, just, I told myself, for a little look. City breaks were there, in Rome and Porto, beach holidays, too, in Cyprus, Malta, the photos are of indistinct turquoise oceans, scattered with mocked-up Polaroids of pyramids and sand. What’s the worst that could happen, I started to ask myself, my finger hovering above the buy now button.

That cynical part of myself would speak up then, in its low exhausted drone, and list all the worsts, in no particular order, from the wet-floored self-catering units overlooking sewage-treatment plants, to the romantic city breaks in active conflict zones, to the buffet breakfasts made up exclusively of ham, and a turbulent plane that is standing room only, arriving at 4am at a holiday resort built hurriedly by enslaved youths. I chose to fade the voice out at some point and think about not just the potentially blissy beaches or affordable wine, but the true gift of the Ultimate Mystery Holiday (a gift that you receive even if you do happen to end up kidnapped by say, the local boys whose families have been decimated by hoteliers’ unlawful practices) which is, that the decision-making is taken out of your hands. Surely that alone is worth £99.

The world is large and holidays are short – yes, you could go back to the sweet bed and breakfast in north Wales where you had that lovely week in 2003, you could do that again and again, and it would be fine, but you will never, let’s be honest, recapture that first shock at the beauty of its landscape, that first feeling of quiet lust you discovered in its yellow bedroom, youth.

Yes you could fly to that Italian island you keep seeing friends go on about on Instagram, but again, sorry, the honesty – you are not built of the same pure jubilance as these friends, nor do you have the same sized wallets, nor, nor are you able to run in a bikini without noisily apologising. And if you want to holiday with friends, you first need to ensure you have made at least one friend who has the patience and particular nous for organising said holiday.

You do not simply arrive at middle age with the efficiency or desire to first calculate the similar-but-different dates when six people can take time off work, then sift through holiday rentals, bearing in mind friends’ budgets, toilet requirements and secret third expectations (associated with nostalgia, fear, exes and alcoholisms), which remain unsaid but have the power to either make or destroy the entire summer.

No, this is a skill years in the making, and one that few, understandably, are willing to take responsibility for. Solo holidays can be preferable, in theory times of grand self-discovery and extensive journalling and “travel”, but more often times of breakfast cocktails and bed at eight. It’s hard to holiday, is what I’m saying. It’s not easy.

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So, I’m talking myself into it now, the Ultimate Mystery Holiday, because: what is a holiday for if not a chance to escape what we already know, a chance to take a week-long risk, throw our little lives in the air like dice? What is a holiday, if not a fine balance: the knowledge it might be awful alongside the slim possibility of gorgeousness? What’s a holiday for, if not the chance for brief, exquisite freedom from yourself? At £99, it’s a bargain.

Email Eva at e.wiseman@observer.co.uk or follow her on X @EvaWiseman

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