THE MYTH OF THE ‘ONCE-IN-A-LIFETIME’ TRIP

The phrase crops up a lot when people are planning a big holiday.

A milestone birthday.

A wedding anniversary.

A point in life where it feels as though this one really needs to count.

And on the surface, it sounds lovely. Meaningful, even. A way of saying: this matters to us.

But over time, I’ve come to think that “once-in-a-lifetime” is a surprisingly unhelpful way to frame a trip.

Not because the trip isn’t important - it often is - but because the label quietly adds a layer of pressure that doesn’t always serve the experience itself.

Why the idea is so appealing

Calling something a once-in-a-lifetime trip gives it weight. It turns a holiday into a marker. It also gives people permission - to travel further, to stay longer, to spend more than they normally would.

That can be a very positive thing.

It can also feel reassuring. If this is the trip, then surely it’s worth the effort, the research, the investment.

The trouble is that the phrase doesn’t just raise expectations - it concentrates them.

When expectations start to work against you

Once a trip is labelled “once-in-a-lifetime”, it can start carrying an unrealistic amount of responsibility.

It has to be:

• the best destination

• the best time

• the best experience

• the trip you’ll always look back on

That often leads to overthinking. Too many moving parts. Too many “just in case” additions. A sense that everything has to be maximised, because there won’t be another chance.

Ironically, this is often when trips start to feel a little strained.

The pressure to get it right can crowd out the simple things that make travel enjoyable: ease, flow, the ability to settle into a place without constantly assessing whether it’s living up to expectations.

What actually makes trips memorable

When people talk about the trips that really stayed with them - the ones they return to in conversation years later - it’s rarely because they ticked every box.

More often, it’s because the trip felt right at that point in their lives.

They felt comfortable. Or rested. Or quietly exhilarated.

They weren’t rushing.

They weren’t second-guessing the decision.

Sometimes the memories are small: unhurried breakfasts, evenings that unfolded naturally, the feeling of being exactly where you needed to be at that moment.

Those aren’t things you can force — and they don’t tend to thrive under pressure.

The quiet truth about “big” trips

Here’s something people don’t always say out loud: most travellers don’t actually want one defining trip that other trips are measured against.

What they want is a relationship with travel that continues to evolve.

Different trips suit different seasons of life. What feels right at 40 isn’t necessarily what feels right at 55. Energy levels change. Interests deepen. Priorities shift.

Seen through that lens, travel doesn’t need to peak. It just needs to keep fitting.

A more helpful way to think about it

Instead of asking whether a trip is once-in-a-lifetime, it can be more useful to ask quieter questions.

Does this suit how we want to travel right now?

Will we enjoy the pace of it?

Trips planned with those questions in mind tend to feel easier and less demanding.

And perhaps most importantly, they don’t close the door on future travel. They leave room for the idea that there can be more — different, equally enjoyable, and just as meaningful in their own way.

Letting go of the label

None of this is about playing down the importance of a big trip. Milestone travel can be wonderful, and it often deserves thought and care.

It’s simply about letting go of a label that can quietly make things harder than they need to be.

The best trips don’t usually announce themselves as life-defining while you’re on them. They reveal themselves slowly, in how often you think about them afterwards, and in how they shape the trips that come next.

If you’re in the early stages of planning a big trip and finding it harder than expected to pin down what feels right, sometimes it helps to talk it through with someone who’s done this many times before. I’m always happy to have an initial, no-obligation conversation to help bring a bit of clarity.

The trips that stay with us are rarely the ones that tried hardest to be unforgettable.