Stop procrastinating and start booking: how to plan your perfect holiday – quickly

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Holiday planning has become increasingly work and time intensive. Isn’t it time we gave ourselves a break?

Words: Nell Frizzell

Not until you’ve dusted off your GCSE atlas at midnight to look up where Abu Dhabi is, as you race against the countdown clock for your booking on the Korean Airlines website (all the while plagued by a nagging worry that your visa won’t arrive in time), will you fully appreciate exactly what a travel agent is for.

Crossing continents and sailing the ocean waves can be a time-consuming, expensive and exhausting business. Which, of course, is why our parents considered it a business – literally someone else’s job. And yet, according to the Association of British Travel Agents, only 17% of us still book our holidays through high-street travel agents. Gone are the glory days of Martha Gellhorn who, upon deciding to explore Africa in 1962, simply invited “a nice young woman, a travel agent, over for a drink”. That’s right, Gellhorn – the woman who dragged Ernest Hemingway around China and chartered her own boat through a typhoon – quietly sat back on her sofa with a whisky, told the nice young woman from the travel agency that she wanted to go to Africa and, lo, “That took care of travel plans.”

The booking journey

For the modern working woman, sadly, things aren’t quite so simple. According to Expedia, it takes us 45 days to book a holiday, making around 35 visits to various travel sites before we finally click pay. We’ve never had so many places open to us – the world is quite literally our oyster. But thanks to cheap air travel, a decent exchange rate and the ability to book flights, accommodation and activities directly, more and more of us are taking it upon ourselves to wrestle with the sweat and dust of travel arrangements, even when doing so can take longer than the break itself. We may consider ourselves sophisticated, well-read globetrotters, but for fear of missing out on a single detail we spend all-too-many precious hours planning every detail of our so-called leisure time like a military operation.

While all this choice should be liberating, it is, in fact, causing us anxiety. “Too much information can create an information overload,” says Dr Benjamin G Voyer, a psychologist fellow at the London School of Economics. “As a result, we become incapable of consciously processing, sorting, prioritising or deciding what option is best. Our mind has evolved to make simple ‘fight-or-flight’ decisions. We have not evolved to be in an environment in which we have many criteria to consider before being able to make a decision. As such, information overload – also called ‘tyranny of choice’ –makes us less capable of making the right decision and often results in us being less satisfied with the decision we made.”

In a recent poll, the travel site Momondo ( found that 33% of women claimed to suffer from stress during the planning stage of a holiday, compared with just 23% of men. Which may prove that women are sweaty-palmed killjoys who can’t even book a flight without seizing up like the Tin Man. Or, more likely, that when it comes to booking the hotel, motel or Holiday Inn, the grunt work more often than not falls to a woman. Because, as our grandmothers no doubt told us, if you want a job doing, you should ask a busy woman. Any woman, in fact.

I’m a woman. So when I decided a few years ago that I would spend three months cycling around New Zealand, to discover the country where my father was born, I naturally assumed it would be relatively easy to piece together each element of the trip, from the flights to the accommodation, myself. On the contrary; it did not go well. Not only did I manage to temporarily lock myself out of my own bank account while attempting to book a flight (full story too harrowing to include here), I also completely forgot that visitors to New Zealand need a visa. And so I found myself, weeks later, standing at passport control, staring blankly into the face of an airport official, mumbling softly about my grandfather’s war record and offering to do a haka. Luckily, after much confusion and panicked whimpering, I remembered that I had brought my New Zealand passport and was eventually allowed into the country. 

The whole experience was enough to put me off holiday planning for some time. Until, that is, my boyfriend and I decided to go on a spontaneous, romantic trip to Berlin last year. And by spontaneous I mean three weeks spent shovelling my way through every restaurant review, every train timetable, every Airbnb user comment and every guide book on the local area available (according to Expedia, we are more interested in review sites in the UK than our friends across the pond in the US). We bought maps, translated weather reports, downloaded exhibition texts and even, at one point, took to Google Street View to plan an early evening walk. The holiday was perfect, of course, even though, or perhaps because, so much of it had been listed on Post-it notes and meticulously sketched out in notebooks before we left.

Be prepared

Despite the rise in anxiety that planning a holiday can induce, some level of planning is a good thing, especially if things don’t go to plan. “Holidays can also be a stressful time, for instance when things go wrong” says Dr Voyer. “Planning and carefully attending to every detail can help us feel more confident that everything will be OK and therefore help us prepare for a relaxing holiday.” 

For 2016 however, I’m bowing out of doing it myself. Later this year, my boyfriend and I are going to cycle across Ireland, from Dublin to Achill Island. As I write, said boyfriend is researching bike hire, rail-and-sail timetables, youth hostels, ferry departures and rain forecasts. While I am off to Lidl to invest in some padded cycling shorts. That’s it. I’m giving myself an entirely different kind of ‘break’ – a break from the booking process. Perhaps it’s time to let someone else do the planning – for me that’s the boyfriend, for you, it could be back to the travel agent. Perhaps delegation is the better part of valour. And perhaps romance isn’t dead after all – it just needed a holiday. And a pair of padded cycling shorts.

How to book a holiday in less than 36 hours

We ask travel industry insiders their top tips for speedy holiday planning.

Tamara Heber-Percy, Co-founder, Mr & Mrs Smith

Let someone else do the legwork to save you time; first of all, create a holiday brief. Write down how far you want to travel, which climate you’d prefer and what sort of a holiday you’re craving and set a realistic budget. Then, send it to a travel company, such as my company, Mr and Mrs Smith, who can send you a few bespoke itineraries. I guarantee you won’t go back to your former holiday-booking ways.

One of the best apps that I use is Travelmath, which calculates drive and flight times, so you instantly know which of the two is quicker. It takes costs and time-zone differences into consideration, effectively cutting down on the boring bits of trip planning.

Where I eat on holiday is important to me, but I don’t like to feel as if the holiday is rigidly structured. So my top tip is to book three restaurants for each night, then decide where to eat on the day. You can easily cancel the other two; it’s so much better than panic-booking at the last minute.

Claire Griffin, Founder of Grifco PR travel company

I have a list of cities and resorts in my notebook with my travel wish list. I look at my work diary and schedule weeks when I want to travel and the best times of year to go to various places. Then in 36 hours I plan the year, book the breaks and slot them into my schedule. 

I often decide on the hotel first, and book direct on their website (this month I’m staying in Rome Cavalieri with views over ancient Rome). For UK breaks, I’ve started using Next I go onto three flight websites to compare prices – Easyjet, Skyscanner and BA. But for a weekend in New York in May, I’m using new airline, La Compagnie (, which flies from Luton and has business class seats at premium economy prices.

For longer holidays I book through an operator – I’m looking at Western & Oriental ( and Hayes and Jarvis ( for a 10-day break to Thailand at Easter. Also this year I’m going on safari – the second week of December is a great week to go as it is a bit more affordable. Yellow Zebra Safaris ( has caught my eye: one telephone call gets this ball rolling for you.

Susan Riley, Stylist’s deputy editor

Plan travel annually rather than trip by trip. Every January I pick eight ‘bucket-list’ locations that I’d genuinely love to visit with the intention of picking two or three. Next I look at my other social and work commitments for the year and slot in where holidays will be feasible before selecting one big trip and two small.  

Phone up specialists for advice, even if you don’t book through them. Trailfinders are brilliant at advising on flight itineraries for multi-stop trips – they simplified my three-week tour of Australia in under 30 minutes. And for roadtrips or tours, check itineraries devised by trusted travel companies such as Audley Travel and Abercrombie & Kent before devising your own. 

I avoid review sites, preferring to stick to three or four accommodation websites that recommend things I love, and for everything else I rely on like-minded and well-travelled friends for tips and recommedations.

Serena Guen, Founding editor-in-chief of

I think about the process of booking a holiday in three distinct sections: deciding, booking and planning. Deciding usually takes the longest. I consider where my friends live first or where they have gone on holiday and the places I can’t stop talking about: west Ireland is next on my list.

If you’re looking for a last-minute deal, Skyscanner’s flight deals are pretty spectacular. If you’re booking in advance, newcomer website Doris and Dicky ( takes all the legwork out of finding affordable boutique hotels. 

But if you’re being spontaneous, you can always find great hotels on the Hotel Tonight app. (Stylist readers can get £15 off by using the promotion code STYLIST – applies to first time bookers on sales over £85.)

Before my departure, I always post a striking image of the destination I’m going to on Instagram or Facebook and ask for tips. 

Images: Getty

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Stylist Team