SINGAPORE, April 30 — With the Labour Day long weekend coming up, and the June school holidays just around the corner, I bet many of you are psyched up for that impending family holiday.

After all, according to accommodation website Hotels.com’s latest Travel And Happiness Index, which was released last week, 85 per cent of Singaporeans feel happy during a trip (and 56 per cent of us feel happiest when anticipating, discussing and planning one). Finally, 57 per cent feel family holidays are our favourite type of trips.

While I agree its fun and gratifying to think about an upcoming vacation, sometimes family holidays can be more stressful than relaxing. And I’m saying this after a very recent experience: I have just returned from an eight-day, multi-generational family vacation in Japan, and it proved to be way more challenging than our usual nearby getaways.

It’s a working holiday

For one, unless you have a travel concierge at your disposal, an extended free-and-easy family holiday is never that free or easy. It requires massive planning and resources.

There are mundane issues like logistics, budget and transportation to sort out. Are the travel dates good for everyone? How many days of school do you want your toddler to miss (if your trip is not during the school holidays)? And how exactly are you going to get around at your destination?

Compromises and trade-offs must be made. My family’s trip to Kyoto involved a harried transfer at Hong Kong International Airport. We decided to take a connecting flight in order to save money. But a 45-minute window to get to the next gate — with hand luggage, a two-year-old, security clearance checkpoints to clear and toilet breaks to factor in — proved nerve-wracking.

We arrived just in time, panting and relieved to have made it.

Similarly, planning an extended family drive-through of Scotland’s Highlands means finding accommodation that can fit 10 people — not exactly the best situation when all you get are tiny beds and breakfast inns in small towns with two rooms to spare.

These are usually just the tip of the iceberg. Wait till you get to your destination and start your itinerary proper. You can always count on the parents to worry or grouse. “Where’s the shuttle?” “Why is it taking so long?” “Where did your sister go? The shuttle is here.”

I now have great respect for tour guides who have to deal with these questions constantly and manage expectations. Things can, and will, go wrong. We had planned to have dinner at a particular izakaya somewhere in the small lanes of Gion, but Google Maps couldn’t locate it and we spent more than 20 minutes searching for it. At what point do you throw in the towel and say, “Forget it, we’ll eat somewhere else”?

These small things get magnified when you’re dealing with fatigue, hunger and grouchiness across three generations. We were also caught in the rain while trying to hunt down our Airbnb apartment in Osaka. Managing three large suitcases while carrying umbrellas and desperately calling our host was possibly the most trying moment of the trip.

Tension in the mansion

Of course, nobody’s perfect and chirpy all the time on a holiday. Least of all children. You bring them to a perfectly fun-looking playground you’ve just discovered only for them to say, “I don’t want to take the slides. I want to go home.”

There were tears and tantrums to contend with in a restaurant. While every Japanese kid in there seemed to be quiet, well-behaved and had perfect table manners, ours spilled a bowl of soup while trying to grab a toy.

I know I am supposed to be more forgiving, and be in a better mood precisely because I was on a holiday. But how could I when my two-year-old was being deliberately annoying while I was trying to enjoy being on a holiday?

Also, there is nowhere you can escape to when things get tense during a trip. It’s not like you could go to work the next day while your father is still upset that you’ve upset your mother accidentally. (Sorry again, mum!) Unlike a holiday with friends or a romantic partner, you can’t abandon your parents and kids in a foreign land to wander off on your own. What’s left to do? You begin anew the next day.

Thankfully, these incidents, while stressful, were all minor in the general scheme of things. Everyone returned to Singapore safe and sound, suitcases bursting at the seams with Pablo cheese cookies and green tea biscuits and iPhones filled with smiley shots.

“You know what, I think we should stick to simpler holidays,” commented my sister. “Like a resort or a cruise.”

I thought about it. Sure, it makes sense to just stick to one place, with minimal exertion. Then again, aren’t the best travel stories and memories made up of adventures both good and bad? There’s nothing like some (contained) drama and spontaneity to remember your trip.

We can look back and laugh when we recall, “Hey, remember that time when we had to walk up and down in the rain with our suitcases for half an hour and we couldn’t find the second bathroom in our Kyoto machiya until our last day?”

Maybe these experiences and reflections are, in our travels, what happiness is really all about. — TODAY