Somewhere between opening the seventeenth browser tab and trying to work out whether a train in another country requires a separate seat reservation, I realised something: Planning a big trip has a way of slowly convincing you that you are both a project manager and a slightly underqualified air traffic controller.

This is not a long weekend or a quick “we’ll just wing it” getaway, but the kind of trip where you start mentally dividing your life into phases (the Nordic phase, the cruise phase, the Berlin phase). The kind where you have spreadsheets. The kind where you know, with absolute certainty, that your future will include dragging a suitcase across cobblestones and praying you don’t lose a wheel. As we started planning our own multi-country, multi-month “gap quarter”, part of my brain focused less about destinations and more about structure.

That became the basis for this series.

Not “how to travel perfectly.”
Not “how to see 14 countries in 12 days while surviving entirely on airport sandwiches.”

Just answering the question: “How do you plan a big trip without slowly driving yourself up the wall?”

(hey, is this summary even too much for you, jump down to my framework)

Note on the cover image: the bronze statue of the crying baby on cover image for this post is from the entirely inexplicable Vigeland Sculpture Park in Oslo.

Part 1: Planning for energy, not just time

This post is about deliberately protecting physical and mental energy, which is paramount on a longer trip. This is a marathon, not a sprint as they say.

We look at various ideas like museum fatigue, laundry, and eating in, and avoiding that ‘I need a holiday after my holiday’ feeling when returning home

Even with the most action packed holiday, it should give everyone space to unwind and not feel too much like ‘work’.

Part 2: Maps before hotels

This post came from a mistake I think a lot of us make.

We choose accommodation based on price or aesthetics before understanding the geography of a place. We fall in love with the idea of a hotel before understanding where our actual life in that city will happen.

But geography shapes almost everything. From transit time to nap time possibilities (I love a good nap and on longer trips especially, this matters more than expected.

A good location isn’t necessarily the most central one. Sometimes it’s the place near the train line that quietly connects all your weird little interests: breweries, museums, vegetarian restaurants, bookstores, late-night convenience store snacks, and one extremely niche attraction you found at 1am while “just quickly checking something.”

Part 3: Booking order matters more than you think

This one was about dominoes. Or perhaps Jenga.

Every booking on a longer trip affects the shape of the next one. And the temptation to lock in exciting things early can create what can be described as “golden handcuff” decisions that feel thrilling at first but become awkward later when everything else has to bend around them.

What surprised me while planning this trip was how much stress comes not from the number of decisions, but from the sequence of decisions.

The most helpful shift for us was learning to book the least flexible things first and letting the rest slot in.

Part 4: The risks we actually plan for

The final post in the series ended up being less about danger and more about fragility.

Because the truth is, most travel disasters never happen.

But some things are worth preparing for simply because they’re difficult to recover from: lost passport, missing wallet, getting sick, and increasingly a lost or damaged phone.

The phone one feels especially modern. Losing your phone now means losing your map, tickets, accommodation details, authentication codes, banking access, and your ability to confidently pretend you know where you’re going.

What we realised is that good planning isn’t about eliminating uncertainty. It’s about reducing single points of failure. The good ole, ‘two is one one’ is none adage.

What I think this series is actually about

At first glance, this series is about planning, but underneath, I think it’s really about reducing friction and identifying where you want to focus your valuable energy and money.

The older I get, the less interested I am in “maximising” travel. I want trips with breathing room. Trips where there’s space to notice things. Trips where I can spend an extra twenty minutes in a library without mentally recalculating the rest of the day.

The irony is that longer trips often look freer from the outside, but they actually benefit from more thoughtful structure, not less. Not rigid schedules, just good bones. And some nice snacks back in the room.

The framework

If I had to boil this whole series down into four ideas, it would be this:

Think about your personal energy first
Before choosing where you sleep, decide where you will live your days
Sequence your bookings intentionally
Prepare for the risks that actually matter

That’s really it.

Not perfection. Just enough structure that the trip can happen without constantly fighting itself. And honestly, I suspect that’s what most of us are looking for in the first place.

Below are links to each of posts if you would like to read more:

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