I once made a colour-coded itinerary for a five-day trip to London. Hour by hour. Restaurants booked for every lunch. A back-up plan for rain, which was itself colour-coded.
I came home tired and slightly resentful, and the bit I remember most fondly is the afternoon the plan fell apart and we sat in a park doing nothing for three hours.
That was the lesson, and it took me two more trips to actually learn it. Here’s what I do now.
Book four things. Only four.
Before a trip, I book exactly four categories of thing:
- Getting there and back. Flights, trains, whatever.
- Somewhere to sleep. Every night accounted for. This is the one I won’t wing.
- Anything that sells out. The one museum with timed entry, the tour that runs twice a week, the restaurant with a three-week list. Usually one or two things total.
- The first morning. Something small and specific for the first morning after arrival, so I don’t waste the freshest day standing on a street corner deciding.
That’s it. Everything else stays open.
The fourth one is the sneaky-important one. Arrival day is when you’re most tired and least decisive, and an empty first morning tends to become a two-hour scroll through reviews in a hotel room.
The three-things-a-day rule
For each day I write down a maximum of three things I’d like to do. Not a schedule — a list. No times, no order.
Three is the number because it’s roughly what fits without rushing, and because if you write five you’ll spend the day watching the clock. If I do two of the three I count the day a success. If I do all three I feel like I’ve won something.
The rest of the day fills itself. It always does, usually with the parts you end up telling people about.
The one-list-per-city trick
Instead of an itinerary, I keep one list per city. Just names and a word each:
Coffee: [name], [name] Food: [name] (lunch, no bookings), [name] (worth booking) Walk: the river bit, the old town, the park with the thing If it rains: the big museum, that covered market
Then each morning I pick from the list based on where I am, what the weather’s doing and how much energy I’ve got. It’s the same research an itinerary requires, minus the tyranny of a schedule that assumes you’ll be in a specific mood at 2pm on Thursday.
I keep it in a single note on my phone. One note. Not forty tabs.
Leave one day completely empty
Every trip gets one day with nothing on the list at all.
It’s always the best day. Every time. Not because unplanned days are magic, but because by day three you’ve noticed things — a street you liked, a café you walked past twice, a shop that was shut — and an empty day is when you go back to them.
If you plan every day, you never get to go back to anything. You just keep meeting new places at speed.
What I stopped doing
Reading every review. Past about five, you’re not learning, you’re just anxious. The sixth review has never changed my mind about anything.
Booking dinner every night. Two dinners booked, the rest walk-in. Being locked into a restaurant across town at 8pm has ruined more good afternoons for me than anything else.
Optimising the route. I used to cluster everything geographically to save walking. Then I noticed the walking between things was frequently the nicest part.
Packing for the version of me who exercises on holiday. She has never once shown up.
A normal day, under this system
Wake up whenever. Coffee from the list. Do one of the three things. Eat somewhere I walked past on the way. Do a second thing, or don’t. Sit down somewhere for an hour with no agenda. Go back to the room and be horizontal for a bit before dinner.
That’s it. That’s the whole method, and it produces better trips than the colour-coded version ever did — with about a tenth of the work beforehand.
The part I still get wrong
I still over-research. I’ll do it before my next trip too. The difference now is that I do the research and then don’t turn it into a schedule — it goes into the one list and stops there.
Turns out I don’t actually enjoy planning. I enjoy the feeling of being prepared. Those are different things, and the one list gives me the second without the first eating a week of my evenings.