IF YOU ASKED ME TO PLAN THREE TAILOR-MADE ITINERARIES THIS MONTH...

People sometimes ask me which holidays I most enjoy planning.

It’s a surprisingly difficult question to answer.

It’s not necessarily the most expensive trips or the most complicated itineraries that excite me. It’s the enquiries where, almost as soon as I put the phone down, ideas start tumbling into my head.

The routes. The little detours. The places I know are going to make someone say, “I’m so glad we included that.”

So, if you asked me to plan three tailor-made holidays this month, these are the enquiries I’d secretly be hoping would land in my inbox.

Argentina: the ultimate jamboree bag

I bang on about Argentina rather a lot.

That’s because it’s my favourite country and, having visited several times, I’m still not remotely finished with it.

Argentina is a bit like one of those old-fashioned jamboree bags: you never quite know what you are going to pull out next, but there’s an improbable amount crammed inside.

There’s Buenos Aires, with its grand architecture, neighbourhood cafés, tango, late dinners and frankly unnecessary quantities of excellent steak.

There’s Mendoza, where the Andes provide a rather dramatic backdrop to the serious business of drinking Malbec.

There’s Patagonia, with glaciers, mountains, lakes and landscapes so vast that they make you feel very small indeed.

Head north-west and Argentina changes again. Around Salta and Jujuy, the scenery becomes drier, higher and otherworldly, with red rock formations, salt flats, cacti and villages that feel a very long way from Buenos Aires. Or the Ibera Wetlands with vast expanses of water that are home to caiman. capybara and numerous different types of birds.

Just when you think Argentina can’t possibly have anything else up its sleeve, it produces another completely different landscape.

And then there’s Iguazú. This is my happy place. I’m heading back again in September and, despite having been so many times before, I already know I’ll spend an embarrassing amount of time simply standing there grinning like an idiot.

No photograph prepares you for the scale, the noise or the sheer power of the falls. You don’t so much look at Iguazú as experience it.

That's what makes Argentina such a joy to plan.

You can create a holiday around food and wine, landscapes, culture, road trips or sheer spectacle. You can combine regions that feel as though they belong to entirely different countries.

The difficulty is never finding enough to include. It’s stopping before the itinerary becomes a three-month expedition.

That’s also why there is no standard Argentina holiday. The right route depends entirely on the time of year, the length of the trip and which parts of this extraordinary country appeal most.

And even then, you’ll probably come home with a list of places you missed.

Return visit to Japan

Tokyo and Kyoto are extraordinary. I wouldn’t dream of suggesting otherwise.

For a first visit to Japan, they belong in the itinerary. Add somewhere quieter, perhaps a ryokan stay or a few nights in the countryside, and you have the foundations of a wonderful trip.

But if you’ve already done that, things become even more interesting.

A second visit to Japan comes without the pressure to see everything you've heard of before you go home. You no longer have to march dutifully from one famous sight to the next, terrified that you may have missed a temple everyone else has photographed.

Instead, you can start with a different question: What did you love most the first time?

Perhaps it was the food, the trains, the contrast between modern cities and traditional towns or the sense that everything worked with alarming efficiency.

Perhaps you came home feeling that, despite seeing a great deal, you’d barely scratched the surface. Which is probably true.

A second itinerary might take you north to Hokkaido, where winter brings snow, hot springs and red-crowned cranes performing their  balletic mating dance.

You might head south to Kyushu; you could explore the sacred landscapes of the Kii Peninsula or spend longer in places such as Kanazawa, with time to enjoy the gardens, old districts and excellent food without immediately having to catch another train.

We could include rural ryokans, smaller islands, quieter coastal towns or simply more time in fewer places.

Japan rewards repeat visits because it gives up its secrets slowly. The first trip tends to be about seeing Japan. The second can be about finding your Japan.

And that's a much more interesting brief.

South Africa: beyond the usual route

Cape Town, the Winelands and a safari make an excellent first holiday to South Africa.

There’s a reason that combination is so popular. Cape Town is fabulous. The Winelands are beautiful. And I’m never going to argue against safari.

But South Africa has so much more to offer if you have the time.

I’d be looking for opportunities to weave in some of the country’s less obvious highlights.

The Drakensberg would be high on my wish list. Its huge mountain walls, deep valleys and wide-open scenery bring something completely different to the holiday. It feels a world away from Cape Town, yet complements it beautifully.

It’s dramatic without requiring anyone to haul themselves up a mountain with a rucksack, which is always a point in its favour.

Depending on the time of year and the client’s interests, I might also look at the Whale Coast, the Karoo or KwaZulu-Natal. They’re all very different from one another and each adds another layer to the journey.

And safari doesn’t have to mean the Kruger. South Africa has some wonderful private reserves, malaria-free options and very different safari experiences, depending on what matters most to you.

The joy of planning South Africa lies in the contrasts.

One day you might be eating extremely well in Cape Town. A few days later you could be driving through mountain scenery, watching whales from the coast or sitting quietly at a waterhole waiting to see what appears.

It can be elegant, wild, scenic, indulgent and occasionally slightly eccentric. Sometimes all before lunch.

So why these three?

Looking at them together, I suspect they say as much about me as they do about the destinations.

I like variety.

I like to plan holidays that unfold gradually and feel different from one stage to the next.

I like trip that have enough moving parts to make the planning interesting, but not so many that the client needs a lie-down afterwards.

And perhaps above all, I like journeys that leave people saying:

“I had no idea one country could offer so much.”

Those are the holidays I most enjoy planning.

So, if you happened to ring me this month with an Argentina itinerary, a second trip to Japan or a South Africa holiday that ventured beyond the classic routes, you would definitely have my full attention.