This Spanish holiday is the first time that I’ve done anything quite like it.
Years ago I had to book through agencies (like when I went to Italy for two weeks when I was at Uni), and for our honeymoon I arranged for a few days in Rome and a week in Sicily (and hired a motorbike) – that was fraught because I was having to deal with any mishaps for the husband as well as myself. This holiday showed that its much easier to deal with Unscheduled Alterations To The Plan when I don’t also have to manage another person’s panic!
Half way through my holiday I found that I was learning things about what kind of holiday I enjoy – and being a software developer and a nerd – I decided to start a Holiday Retrospective Board on Trello!
In software development, a retrospective is where the team looks back after a project and asks what worked, what didn’t, and what to change next time.
This is what I captured:
🧪 What Worked
- Multiple stops felt like several holidays.
- Bus travel was enjoyable.
- Countryside views were a bonus.
- Less planning created more freedom.
- Avoiding tourist hotspots reduced queues.
- Unexpected discoveries were often the best moments.
⚠️ Friction
- June heat was exhausting.
- Too much waiting around before travelling.
- Heavy bags in the hottest part of the day.
- Ticket planning mistakes.
- Took too many shoes (I only needed one pair – I took 3).
- Missed several Pride events.
🔁 Next Time
- Travel in May.
- Travel earlier in the day.
- Carry more cash.
- One pair of shoes.
- Check Pride dates first.
- Keep planning deliberately light.
💡 Hypotheses
- Heat magnifies every other problem.
- Less planning encourages serendipity.
- Several short stays beat one long stay.
- Timing matters as much as destination.
- Novelty improves memory.
🧭 Principles
- Phone out of sight.
- Memorise routes.
- Look up and around.
- Carry water.
- Double-check connections.
- Remember to enjoy wandering.
- Cáceres
- Guadalupe
- Cartagena
- Bohonal de Ibor
- Málaga flights from Bournemouth
When I have finished my scrapbook, I’ll start thinking about the next holiday – not planning, just enabling my mind to think “this time I might do x” and knowing that whatever I don’t do next time I can do the time after that!
Perhaps the biggest lesson wasn’t about Spain at all. It was that the perfect holiday isn’t the one where you see everything. It’s the one that leaves you looking forward to coming back.
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