The year I stopped planning trips

There was a time when I planned holidays like a wedding. I had a spreadsheet with tabs. One tab was called “Backup restaurants”. I am not proud of this, but I think it’s important to be honest about where we start.

The spreadsheet years produced some lovely trips, to be fair. They also produced a version of me who stood outside a closed museum in Seville at 10:04, red-faced, because the plan said 10:00 and the plan was law. Rosie, who was with me, ate an orange on a step and waited for me to calm down. It took a while.

Only the first night

The change wasn’t a grand decision. In the spring of last year I was copy editing a long, dull report on freight logistics and simply didn’t have the energy to research a trip to the Alentejo. So I booked one night in Évora, packed a bag, and told myself I’d work out the rest on the bus.

I didn’t work it out on the bus. I slept on the bus. But on the first evening the woman who ran the guesthouse — Dona Lurdes, seventy-something, with reading glasses on a beaded chain — asked where I was going next. When I said I had no idea, she looked delighted, wrote the name of her cousin’s place in Monsaraz on a napkin, and phoned ahead.

That’s more or less how the whole year went. One night booked, the rest handed to me by strangers, bus timetables and weather. In Monsaraz I stayed three nights instead of one because the light on the lake at seven in the morning was the colour of weak tea and I wanted to see it again. I spent €14 a night. I never once looked at a review.

When I went up to Porto in the autumn, I booked the first night and nothing else, and it turned into the slowest, best weekend I’d had in ages.

What I pack instead of a plan

Not planning is not the same as not preparing. I’ve learned to bring a few things that make the gaps easier to live in:

• A paperback I don’t mind leaving behind, usually from the stairwell shelf at home.
• A notebook with the name of my first night’s address written on the inside cover, in case my phone dies.
• Enough cash for a bus, a coffee and a pastry — the holy trinity of rural Portugal.
• A jumper, even in July. Especially in July.

The other thing I pack is a slightly lower bar. If a day turns out to be mostly sitting in a café in Estremoz watching a man repair a moped, that counts. Some of my favourite photographs from the year are of exactly that sort of nothing.

What I lost, and what I didn’t

I won’t pretend it’s all sunshine. I have missed things. I arrived in Tavira the day after a festival ended and walked through streets still strung with paper flowers, everyone hungover and sweeping. I once slept in a room above a bar in Beja that played the same Roberto Carlos song until two in the morning.

But I lost much less than I expected. What I gained was the feeling of being in a place rather than checking it off. Plans are a way of meeting a town halfway before you’ve even arrived. Without one, the town gets to introduce itself.

I still book the first night. I’m not a lunatic. Arriving somewhere in the dark with nowhere to sleep is a story I’m happy to hear from other people. But after that, I let the napkins decide.