THE HIDDEN WORK BEHIND PLANNING A TAILOR MADE HOLIDAY
- sueaitken7
- Jul 3
- 4 min read
The itinerary is the bit my clients see. The hidden work is everything that happens before it.

People sometimes ask me what actually goes into planning a tailor made holiday.
It's a fair question.
From the outside, it can look deceptively simple. Choose a destination. Find some flights. Book a few hotels. Add a couple of excursions and away you go.
If only.
The reality is that most holidays don't become complicated because of one big decision. They become complicated because of lots of perfectly sensible little decisions that all start bumping into one another.
A recent enquiry for Japan is a good example. The clients wanted to see Tokyo, Kyoto, Hiroshima, Miyajima, Fukuoka and Kamakura. Every destination had earned its place. One was there for the floating torii gate, another for the reclining Buddha, another because they'd always wanted to spend time by the coast.
Individually, every idea made perfect sense.
The challenge was turning them into a holiday that didn't involve unpacking a suitcase every other morning and becoming unexpectedly knowledgeable about Japanese railway stations.
Joining the dots
This is where holiday planning stops being about destinations and starts becoming about the spaces between them.
On paper, that Japan itinerary looked wonderful.
The only slight snag was that somebody had to join all the dots together.
This is usually the point where I find myself with several supplier websites open, a map spread across my desk and a notebook full of scribbles that made perfect sense half an hour ago.
Was the original itinerary do-able? Absolutely.
Would it be the best holiday for my clients? That's a much more interesting question.
Sometimes adding another destination makes a trip richer.
Sometimes removing one does exactly the same thing.
Working that out is where much of the hidden work happens.

Every holiday has a different challenge
Of course, not every enquiry is about pace.
A family recently came to me wanting to experience a South African safari.
Like many people, their first thought was the Kruger National Park.
It's an obvious choice and deservedly famous.
The difficulty wasn't Kruger. It was fitting Kruger into the family's budget without compromising the rest of the holiday.
Once we'd looked at the alternatives, Pilanesberg National Park emerged as a much better fit. It would still give them an outstanding safari experience while leaving enough in the budget to create a more balanced holiday overall.
Sometimes the best destination isn't the most famous one. It's the one that's right for that particular holiday.
Then there was the couple who wanted two apparently unrelated things: to explore Vietnam in depth and to experience a river cruise.
Rather than bolting a week's cruise onto the itinerary, we found a much neater solution – a short Mekong cruise linking Vietnam and Cambodia.
They’ll still experience life on one of Asia's great rivers, but it’s become a natural part of the journey rather than feeling like an add-on.

It's the little things that make the difference
Many of the decisions I make are surprisingly small.
Would changing the order of the itinerary reduce travelling?
Is another hotel change really worth it?
Sometimes the details are even more practical.
One recent enquiry involved two ladies travelling around Japan with mobility scooters. Finding accessible hotels was only part of the picture. The harder questions were things like whether a station had lifts, whether the hotel was at the top of a hill and whether saving half an hour on a train journey was really worth another hotel change.
Google Maps, incidentally, is wonderfully optimistic. It has an uncanny habit of making everything look ten minutes away. It occasionally neglects to mention the hill, the steps or the fact you're manoeuvring a suitcase in 30-degree heat.
None of these decisions is particularly dramatic on its own.
Collectively, they're often the difference between a holiday that feels effortless and one that feels hard work.
So where do we start?
If you've got a notebook full of ideas, a rough budget and a growing suspicion that fitting everything together is proving a little more complicated than you'd expected, that's exactly where I can help.
Sometimes the answer is changing one destination.
Sometimes it's slowing the pace.
Sometimes it's discovering a solution that hadn't occurred to either of us.
If I've done my job well, you'll never know about the hotel that quietly disappeared, the route that changed three times or the conversation that transformed the itinerary.
You'll simply come home saying, "It all flowed so naturally."
And, for me, that's probably the nicest compliment there is.
Ready to start planning?
Whether you've already got a clear idea of where you'd like to go or you're still weighing up the possibilities, I'd be happy to help.
The first step is simply a conversation. We'll talk through your ideas, your budget and what's most important to you, then see whether we're a good fit. Get in touch to arrange an initial chat.




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