Slow Travel and the Art of Not Having a Plan
For most of my traveling life, I planned obsessively. Not in a neurotic way — or maybe in exactly a neurotic way — but in a way that felt like responsible travel. Spreadsheets. Saved Instagram locations. A Notion database of "things to do in X city" with tags and priority ratings.
The trip to Portugal broke me of this habit entirely.
How It Started
I had four weeks between jobs — one of those rare life windows where obligations temporarily evaporate. I bought a one-way ticket to Lisbon and booked exactly one night of accommodation. A friend thought I was having some kind of episode. Maybe I was.
What actually happened: I spent a week in Lisbon without moving, because Lisbon is the kind of city that rewards staying. I found a café near the top of the Alfama hill that had good espresso and an outdoor terrace, and I went there every morning and wrote. I walked until my feet hurt, then walked more. I learned the tile patterns of different neighborhoods. I started to understand the city's grammar.
The Alentejo Detour
On a Thursday, I asked a woman at my guesthouse where she would go if she had a week and no plans. She said the Alentejo, without hesitating, and wrote down the name of a small town I'd never heard of. Population 3,000. Cork oak forests. A medieval castle. One restaurant that opened at 8pm and closed when the owner felt like it.
I took the bus the next day.
The Alentejo is what Portugal looks like when the tourists haven't arrived yet. Ochre plains, wildflowers, whitewashed villages with blue-trimmed doorways. The pace of life felt like a different metabolism. I stayed four days intending to stay two.
On the Philosophy of Slow Travel
Here's what I learned: most of what I remembered from previous trips wasn't the sights I'd optimized for. It was the accidental stuff. A conversation with a stranger who insisted on buying me a beer. Getting lost and finding a square with a fountain and kids playing football. The specific quality of afternoon light through a curtained window.
You don't find these things on a spreadsheet.
Slow travel isn't lazy travel — it requires its own discipline. The discipline of sitting with boredom until it becomes curiosity. The discipline of not reaching for your phone every time you're uncertain what to do next. The discipline of trusting that interesting things will happen if you leave space for them.
What I Brought Back
Three things that have stuck with me since Portugal:
The morning walk. I now walk every morning before looking at email or opening a laptop. It's the closest I've found to that café-on-the-hill feeling in ordinary life.
The one-restaurant rule. When I'm somewhere new, I find the place that's been there forever and go twice. The second visit is always better.
The question. I ask locals where they would go, not where they send visitors. The answers are almost always better.
Portugal is waiting if you want it. Take fewer plans than you think you need.