I don’t know how you feel about holiday planning. I can’t do it too early, but my wife is more impatient. So last week we did some holiday planning and it went like this .
Her: “We’re going to Lisbon in three weeks time, don’t you think we should do some planning?”
Me: “Okay let’s do it now. I plan to get on a plane and fly to Lisbon. Then I plan to book into our Air b’n’b. Then I plan to have a good time for a few days. Then I plan to fly home. All done.”
We are quite different when it comes to travelling. Once we have booked flights and accommodation with several months to go, I put the whole thing mentally to one side, and only really get into it a couple of weeks before. Or even days before. Or sometimes on the plane itself if we have been really busy in the days leading up to our departure. My soul mate by contrast makes lists, buys guide books, researches on the internet, and rings up every friend and colleague who she knows has visited our destination in the past. She will even stalk the neighbourhoods of where we are going on Google Earth street view, peer through the windows of shops and press her virtual nose to the glass of eating establishments. Okay I may be exaggerating a little there. But she is a great one for preparation.
My big fear in this highly sophisticated information world of ours is that if you over-prepare you lose the pleasure of the naive experience. Naivety has a lot to recommend it when travelling, personal safety notwithstanding. I would rather find out about a city from a barman than a guide book or from a barista rather than from Google.
A good way of getting to know a country, but not one I would recommend, is to use its healthcare system. Some years ago a family member we were travelling with ended up in a Tel Aviv hospital for a week with a serious medical condition. For the record it had a happy ending, but in between times we (and particularly my wife who bore the brunt of it) learned a lot about how to get by on a daily basis in a city where the emphasis was on endurance rather than enjoyment.
Alternatively you could try being stranded somewhere for a week due to an act of god. In 2010 the eruption of an Icelandic volcano caused a shutdown of European airspace. It blew up – literally – when we were flying back from Australia and were having a short stopover in Singapore. Suddenly all the indicator boards for Europe went FLIGHT CANCELLED and we found ourselves stranded. We spent the first night sleeping on the transit lounge floor whilst confused airline officials put operation headless chicken into effect by way of a business continuity plan. The different phases of this ran as follows. First denial – “no worries, we’ll be on our way again soon”. Then confusion – “we’re not sure what’s happening, here is a meal voucher and a blanket”. Then came the phase known as “the shit has hit the fan but we don’t have a plan”. More meal vouchers and a promise that everything will be okay. Meanwhile the stranded passengers started forming into groups, lighting camp fires, singing Kuymbaya, swapping email addresses, hugging and crying, and sharing toiletries and biscuits. A few rich unworthies sneaked off and booked into the transit hotel. Treacherous bastards. We explored the airport, made contingency plans, and declined the offer of going to the showers in small groups. Eventually we were whisked off in taxis to a hotel and were put up there by the airline at their expense.
This was a whole other experience. First off nearly everyone in our hotel was from a different flight. Their experience had been pretty awful in that they actually flew two hours out of Singapore before being turned back and landing where they had started. Our sympathy for them cooled rapidly however as they went full Lord of the Flies on us and made it clear we weren’t welcome to join their meetings with airline officials or socialise with them in any way. We ignored the former request and went along. As to the latter, we formed a tribe of three and ignored them back. There was one interaction however that remains vivid in my mind. I dabbled with yoga in those days and got up on the first morning at eight o’clock to do a few exercises by the pool. A generously proportioned young woman was sitting on a recliner stuffing her face with pringles.
“Oooh” she said. “Are you doing yoga? I love yoga, I’ve got a friend what does it”. She then proceeded to stuff the whole tube of pringles down her throat whilst I tried not to fall over on one leg or make a spectacle of myself with a very downward dog that would result in my slipping into the pool.
We had a week of this. It was one of the unhappiest travel experiences of our life. We weren’t short of money and most of our expenses were covered by the airline or by our insurance. Work told us not to worry as there were lots of other people in the same boat so we weren’t under any obligation to check emails and remote working as we know it today was in its infancy. My wife was interviewed by Radio Four and gave the British Embassy a roasting on the airwaves for being so useless. As far as they were concerned we had a roof over our heads, food in our stomachs and weren’t being held at gunpoint so they didn’t care. They certainly didn’t see it as their job to keep us informed. So we went to a couple of theme parks, ate out, did some shopping and read the news obsessively. My laptop was our lifeline and Facebook, which we had not used much until then, suddenly became vital in terms of staying in touch with family and friends. Someone I knew innocently said that it was nice in the UK now as they could sit in their garden without planes flying over. I ripped into them and told them they were selfish and they unfriended me, probably out of sheer terror at my reaction and afraid that I would bang on their door as soon as I got back to the UK and demand satisfaction. Early lesson in social media anger and how it can get out of hand. On day five our son, aged twelve, started crying into his meal one evening because he missed home and friends. Our son and daughter back in England, aged nineteen and seventeen respectively, were desperate to get us back. On day six the airline moved everyone into Pontins style chalets on the outskirts of the city to save money. We told them to stuff it and booked into the Swiss Hotel at what we thought was going to be enormous personal expense, but fortunately the skies were opened the next day and my wife bludgeoned us onto the first plane out. She had to use her highly developed assertiveness skills (which are not far off those deployed by Black Widow in the Marvel movies) to achieve it, and we also had the misfortune to be sharing the plane with the Lord of the Flies Gang; but on landing the plane erupted into applause and cheering and we all went our separate ways.
So in my view it is not worth over-planning a holiday. You never know what it will be like and if you don’t have expectations you won’t be disappointed.

