Once, I prepared a public talk that was playfully titled Planning A Spontaneous Vacation. My colleagues and I had fun with the concept but soon enough an editor asked: “Oh, is there a mistake in your title?”

The underlying question was: “Can you really plan, yet stay spontaneous?”

Being word lovers, our journalistic compromise was a sleight of hand with the punctuation. We simply added quotation marks so our new title looked a little less contradictory: Planning A “Spontaneous” Vacation.

In the same spirit, my talk at the Central Public Library on vacations was scripted, with lots of room for improvisation. I hoped to convey the equal importance of planning and spontaneity in travel. We plan, then go off-script, carefully or merrily, in travel as in life.

That ethos is embraced by essayist and novelist Pico Iyer, whose latest book is the memoir-travelogue The Half Known Life: In Search Of Paradise (2023), where he recounts luminous journeys in Iran, Japan and elsewhere.

Being such a purist explorer, mostly travelling alone and revelling in back streets or remote vistas, it is easy to imagine him as all free spirit. But he is a planner.

“I do enjoy planning. I am fairly organised. It is one of my relative strengths,” he once told me in an interview.

It is helpful psychologically to map out an itinerary, he felt, even if he later departs dramatically from it. “The planning is what allows me to do without the plan,” he said.

Seniors travel spontaneously

I thought of Pico Iyer again when Skyscanner reported recently that 63 per cent of Singaporeans plan every detail of their trips ahead of time, but are equally willing to change their itineraries if they come across a better deal.

Among those who are spontaneous and will change their travel plans on the fly, Skyscanner observed that those aged 65 and above (36 per cent) scored the highest, outranking other age groups.

The appetite of seniors for spontaneity is more than twice as much as that of Gen Zs (16 per cent), for comparison.

“Singaporeans are generally careful planners, but they have a spontaneous side too,” Ms Cyndi Hui, Skyscanner’s travel trends and destination expert, elaborated when I e-mailed her about the Travel in Focus 2023 Report.

“In their golden years, many seniors are eager to embrace impromptu adventures and seize opportunities as they arise,” she added.

In a country that is approaching super-aged status, this is happy news. Spontaneity and flexibility, in journeys and in daily living, awaken the mind to new possibilities and condition the spirit to be ready for the unexpected, good or bad.

Planning is a national forte, and this drills down into the itineraries of my friends and acquaintances, young and old.

Author Koh Buck Song’s wife did epic planning for their round-the-world trip, just before the pandemic. They traversed terrain of great contrasts, ranging from the desert skyscrapers of Dubai to Kenya’s safari world, which he distilled into his book Around The World In 68 Days: Observations Of Life From A Journey Across 13 Countries (2021).

In our recent conversation, Mrs Koh indicated that she is a maximalist planner, which allows her to stretch limited leave to the fullest. She figures that in five years, when she is closer to the golden years, her itineraries will be more chill.

Millennial planners

A-to-Z planning is even more ingrained in Singapore’s young people, who are taught to plan and project from an early age. They are also a digitally empowered generation that has every trip-planning tool at their disposal.

“Millennials are planners,” a colleague said. Not long ago, when her daughters were aged 19 and 22, they both planned every luscious detail of their Bali family holiday, from where to dine to which villa to rent.

Planning is great. But there are times when less is exceedingly more.

I think about film-maker Royston Tan, who once mentioned: “Many times, I carry my passport with me. I like very spontaneous trips.”

On a whim, he had decamped for nearby places like Malacca and Bangkok, where the storyteller found inspiration for his films, whether he was marvelling at old buildings or chatting with a tearful stranger at the bar.

Like him, when I drop the script, I have found priceless experiences and a new level of creativity.

On the last seven days of a month-long Greek odyssey, my travel companion and I were offered free ferry tickets to far-flung Kastellorizo isle, an unknown to us.

When we arrived, we had no problem finding a clean, airy room at an inn whitewashed to a dazzling sugar-lump white, Greek-style.

The island was so near Turkey, which was aspiring to European Union membership, that the Greek islanders taunted their geopolitical rivals with a sign in town that declared: “Europe begins here.”

We were told there was recent sniping in the hills. But our island experience was dreamy, and we encountered a different Greece from Athens, Corinth or Santorini.

Even at night, the water on this secret island was a see-through cobalt. Once, our new Greek friends took us lobster-hunting at midnight for the freshest feast the next day. When we flew off, a sheepdog cleared a flock from the microscopic airfield.

Enigmatic countries, resplendent weddings

Though I plan every work trip meticulously, some of my best stories emerged when I went off-itinerary.

During a high-speed-rail adventure in China, my photo-journalist colleague Ashleigh Sim noticed that the elaborate train system led to the doorstep of North Korea and off we went.

From the Chinese city of Dandong, we spied enigmatic Sinuiju in North Korea. The Yalu River separates the two border cities, and they are only metres apart at the closest point. A sign said: “One Stride Across”.

We caught glimpses of North Korean boatmen, a woman washing at the river’s edge, farm patches, and a cigarette factory. That was the closest we could get to the hermit state without a visa.

It also left me pondering: same countryside, different nations and divergent fates.

And since I am finalising this column en route to Shanghai, other memories of China, which I view as an often gumptious nation with room enough for winging it, are resurfacing.

There was the time I politely gatecrashed a resplendent Tibetan wedding and it was a portal into a joyous, hidden China.

It was my first morning in secluded Shangri-La city, nestled near the Himalayas, and our car was circling a Buddhist stupa.

I spied two young men, stylish in leather jackets, who were firing crackers into a red barrel atop a pickup truck.

They are off to a wedding, our driver said.

An Alice-in-Wonderland moment was conjured up when we trailed the truck to a small hotel, where the bride and groom soon emerged from a limousine adorned with miniature woolly yaks and silk.

With my two Singaporean companions, I mingled with guests clad in vivid garments, the men bearing silver daggers.

Trays of snacks were passed around, and I savoured the fragrant roasted barley harvested from highland fields.

Plans unspool, magic happens

Other times, spontaneity is forced upon us. Travel is inherently unpredictable, and our best-laid plans can unspool in a flash.

That happened in the past when our camper van overturned in New Zealand, and the four of us, then in our 20s, reworked our trip on the go. Not easy, but it was liberating to lose the calendar mindset and live in the moment.

That is why we vacation in the first place, when I think about it.

Go ahead to plan, I say. I take pleasure in that too, not least because I cannot return without a travel story. And without a semblance of a plan, we may waffle away a morning at our Airbnb.

But for the times when we yearn to live a little more spontaneously, here are some possibilities.

Technology is a friend, even if it tempts us to over-plan a journey. Say, a traveller is intrigued by a long queue at a museum not on his artfully curated list. He can still book tickets on a platform like Klook on the smartphone, get instant confirmation of the purchase, and zip into the attraction.

Skyscanner has an Explore Everywhere search tool that ranks destinations by price from the traveller’s origin city. It appeals to travellers who embrace flexibility and are looking for a good deal.

“By presenting a wide range of options, it allows travellers to explore exciting new and off-the-beaten-path destinations that fit the budget they have in mind,” says Skyscanner’s Ms Hui.

Globally, 56 per cent of travellers who search on Skyscanner are browsing prices with no fixed destinations or dates in mind. So, you may get exotic suggestions like Zagreb in Croatia or Nadi in Fiji.

Love cafe-hopping? Local neighbourhoods? Choose an area that’s great for coffee, or an enclave such as the Little Tokyo of Dusseldorf, then explore around it.

My former colleague Lydia Vasko, who was a travel correspondent, advised: “Have some benchmarks, such as a must-go restaurant or attraction. Then plan a free afternoon within your packed itinerary.”

But isn’t it tough for families with young kids to stay spontaneous? A relative, who unfailingly squeezed in four vacations annually when her kids were of school-going age, said: “If it’s a five-day trip, the last two days can be less planned.

“Ask the kids what they want to do.”

Their son, when he was little, ardently planned their city routes in Europe, including how to navigate waterways in the Netherlands, to get to places he fancied such as a train museum.

Given the chance to fill an open itinerary, he took charge. That was a gift of trust and independence from his parents, for life.

Even little ones, and those allergic to being plan-free, can plan spontaneous vacation moments and delight in what happens next.