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Why is it so hard to book a holiday? | Life and style

ohSummer is here again and I’ve forgotten about booking a vacation. I don’t know how you guys do it, how you all do it before you know what you want, with diaries and dates and savings and cat care and all that. It’s not that I don’t want enough. I want more than enough. My inner vacation clock starts ticking back to the bleak midwinter of fantasies of beaches and fresh fish, but as the clock ticks, the rest of me remains motionless, frozen in indecision and lack of imagination.

I realize now that this is probably a time when you’re booking time off work, or looking for a place to rent near the beach, or negotiating which group of friends you can move in with for a week without upsetting any old relationships, or which of your friends’ kids you can move in with for a week. I probably shouldn’t say that. Good. Good.

As I’m scouring the web for places to take the family over the school holidays, I keep finding myself drawn to something online called the Ultimate Mystery Holiday. You may have seen it, or perhaps even seen it in your dreams before you fall asleep, hearing a quiet knock and opening the door just a moment before the mystery appears in your waking dreams too. The Ultimate Mystery Holiday is an option on a popular voucher site where you can buy an “Ultimate Mystery Getaway from £99 per person” along with a compost bin and cream tea.

It goes on to say: “Destinations include Bali, Mexico, New York, Dominican Republic, Iceland, Italy, Egypt and more!” When I first saw this online, my worldly cynic nature born of a lifetime of failure led me to assume that purchasing the voucher would mean a two-week holiday to a little-known resort called & More. But I kept coming back to the website and telling myself to just have a look. There were city breaks in Rome and Porto, beach holidays in Cyprus and Malta, with photos of hazy turquoise waters and faux Polaroids of pyramids and sand. What’s the worst that could happen, I asked myself, as I hobbled my finger over the buy now button.

At that moment, in a weary, low voice, the cynic in me would list all the worst things, in no particular order, from a self-catering unit with a wet floor overlooking a sewage treatment plant, to a romantic city break in a war zone, to a ham-filled buffet breakfast, to a turbulent, standing-room-only flight arriving at 4am at a resort hastily built by slave youth. At some point, I would fade that voice out and think not just about the blissful beaches and affordable wine, but about the real gift of the ultimate mystery holiday (a gift you can receive even if you end up kidnapped by local boys whose families have been taken from you by the hotelier’s illicit activities): the decision-making being taken out of your hands. Surely this alone is worth the £99.

The world is big and holidays are short. Yes, I can go back to that lovely B&B in North Wales where I spent a lovely week in 2003, I could do so again and again, and that’s fine, but I can honestly say that I will never again feel that first shock of the beauty of the landscape, that quiet desire and youth I first felt in that yellow bedroom.

Sure, you could fly to that Italian island your friends are always talking about on Instagram, but then again, let’s be honest: you don’t have the same pure joy or the same sized wallet as those friends. or Can you run around in a bikini without yelling and apologizing? And if you want to go on vacation with friends, you first need to make at least one friend who has the patience and special knack for planning that vacation.

Just because we’re middle-aged doesn’t give us the efficiency or motivation to first calculate the disparate dates that six people can take time off work, then sift through vacation rentals while keeping in mind friends’ budgets, bathroom needs, and the expectations of some unspoken but secret third party (related to nostalgia, fear, ex-lovers, and alcoholism) that have the power to make or break our entire summer.

No, this is a skill that takes years to develop, and understandably few people are willing to take on the responsibility. Solo travel may be desirable in theory as a time for epic self-discovery, extensive journaling and “traveling,” but for many it’s just breakfast cocktails and bedtime at 8 o’clock. What I’m trying to say is that taking vacations is hard. It’s not easy.

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So I’m now about to treat myself to the ultimate mystery holiday. Because what is a holiday if not a chance to escape what we already know, to take a risk for a week and throw our little lives up in the air like a roll of the dice? What is a holiday if not a slight balance between the knowledge that it might be awful and the possibility of it being wonderful? What is a holiday if not an exquisite chance to temporarily free yourself? At £99 it’s a bargain.

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

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