Itineraries Are a Recipe for Missing the Point

How overplanning low-key erases the best parts of travel

There are (roughly) three types of travelers in the world:

1. the itinerary people: spreadsheets, pins, time blocks, backup plans for the backup plans, every little detail picked out in advance

2. the wing-it crowd: vibes, caffeine, one too many cafés for a glass of wine, trips unfolding by divine intervention

3. the “just drop me at a resort or on a ship and don’t ask questions while I enjoy another umbrella drink” contingent (no shade, just… not my lane)

I’ve spent most of my travel life somewhere between the first two.
But here’s the nuance that I don’t always perfectly express when I’m telling my travel story:

Yes, I’m a list person.
Just… not a list of must-see-sites person.

My type of lists were never “Mona Lisa at 10:15, Colosseum at 2:30.”
They were countries. regions. routes. how far the map could stretch if I challenged it hard enough.

I liked the macro challenge. The puzzle. The obsession.
Which is probably how I ended up in every country on Earth without ever caring that much about standing in line for the same photo everyone else already has.

And over time…slowly, stubbornly…I learned something important about myself:

You can absolutely do travel.
But if you’re not at least a little deliberate about it, you won’t actually experience it.

The Acropolis doesn’t need hype. It needs a pause…and the realization that you’re borrowing space from history, not conquering it.

The problem with checklist travel isn’t that it’s wrong.
It’s that it quietly turns travel into somewhat of a job or a chore.

You move fast. You collect proof. You optimize.
You feel productive…which, honestly, is very on-brand for modern life.

But the moments that stay with you?
They almost never happen on schedule.

They happen when you sit too long at a café and chat up a group of students who want to improve their english.
When a “quick stop” turns into a conversation with the eccentric old man and his tiny dog who live down the street and want to tell you every detail of their life in this neighborhood.
When you’re not rushing, not documenting, not mentally checking the next box.

The wild part?
Most people’s favorite travel memories don’t involve the thing they planned hardest.

Nobody comes home glowing about:

• the hours in line

• the crowds

• the timed entry ticket they fought for online

They come home glowing about people.
About stories. About moments that were never anticipated or planned for.

The Great Sphinx of Giza has been watching people rush past it for millennia. You don’t need to be one of them.

And yes, before anyone panics, landmarks are incredible. They’re iconic for a reason.

Standing in front of something ancient, iconic, almost mythic? Still hits. Still slaps hard.

But here’s the quiet shift that happens once you’ve traveled enough and done a bit of introspection about why you love to travel:

Seeing becomes easy.
Being present becomes the flex.

The internet has made visuals cheap.
What it hasn’t made cheap is genuine human connection.

You can Google a photo of anything.
You can’t Google what it feels like to linger somewhere long enough to let it sink in and become part of the local tapestry.

The Great Pyramid of Giza has been here for thousands of years. It’s not on a countdown. You are. Try something different.

This is usually where someone says,
“But if I don’t plan, I’ll miss everything.”

Here’s the reframe:
You’re going to miss things. Always. That’s part of life.

You could live in one city for a year and still miss things. I lived in the Washington, D.C. area for 30 years and there’s still a huge list of things I’ve never seen.

The goal isn’t completion. The goal is depth.

Ask yourself this instead:
Do I want to feel like I did this place…or like I met it and lived it?

Because the deeper travel gets, the less it’s about trophies and the more it’s about texture.

Christ the Redeemer is iconic, sure. But it’s the city below: chaotic, alive, human — that gives the moment gravitas.

Nobody leans in when you say, “I checked off everything.” (well, maybe a little)

People lean in when you say:

• “I met this person who…”

• “We ended up somewhere totally random…”

• “You won’t believe this shit…”

That’s the travel glow.
That’s the stuff that rewires you.

Saint Basil’s Cathedral looks like a fairytale. You don’t need to speedrun the story.

So… are itineraries a good idea?

Sometimes. For some people. On some trips. Or at least some parts of some trips.

But if you want travel to feel expansive instead of exhausting, here’s the move:

Think of your itinerary as a loose framework, not something that dictates every move you make. It should give you a sense of direction without boxing you in or rushing you past the moments that actually matter.

Leave room for the trip to clap back at your expectations.

The Arc de Triomphe is impressive. So is choosing to wander instead of conquer.

5 hot tips for traveling beyond the checklist

1. Anchor, don’t overload.
   One meaningful plan per day. Everything else is gravy.

2. Demote must-sees to cameos.
   Let landmarks be part of the day, not the whole plot.

3. Live where locals live.
   Residential neighborhoods > tourist cores. Always.

4. Schedule nothing (yes, literally).
   Protect unplanned time like it’s sacred. It kind of is.

5. Measure trips in stories, not stamps.
   If you come home changed, you did it right.

The Sydney Opera House is stunning, but the real win is letting the day unfold without micromanaging it.

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