I thought I had the whole "Italian driving" thing sussed after a week in Tuscany last year, but Puglia had other ideas. We'd barely collected our hire car at Brindisi when I confidently followed the sat nav down what I can only describe as a lane designed for determined goats. My partner, Rob, was gripping the door handle like his life depended on it, and our seven-year-old in the back had already started her "are we nearly there yet" routine before we'd even left the airport perimeter. The olive trees scraped both wing mirrors simultaneously, which takes a special talent, and I had to reverse three hundred yards past a nonplussed farmer who clearly found my panicked waving deeply entertaining.

By the time we spotted the actual road to Porto Cesareo, I was ready for something to go right. And it did, spectacularly.

The villa sat behind a low stone wall with bougainvillea spilling over it like it had somewhere important to be. White-washed, compact, utterly unpretentious. Rob raised an eyebrow when he saw the outdoor shower - "very rustic" - but I was already through the door, and the smell of jasmine from the garden hit me before anything else. The place smelled like someone had bottled a proper summer and left the lid off.

We dumped our bags with the enthusiasm of people who'd been in transit since four in the morning and did what any sensible family would do: wandered without purpose. This, I should say, is not my usual style. I'm the woman with the spreadsheet, the restaurant reservations, the "must-see" list colour-coded by proximity. But something about that first afternoon made the list feel ridiculous. The sun was too warm, the light too golden, the narrow streets too inviting.

We turned left where we should have gone right, down a passage barely wide enough for two people passing, and found ourselves in a tiny piazza where an old boy was selling cherries from a plastic bucket. No stall, no sign, just him and a folding chair and a surprisingly fierce-looking cat. The cherries were the darkest red I'd ever seen, and he insisted on filling our paper bag until it threatened to split, all for five euros and some elaborate hand gestures about his nephew's wedding. We ate them walking, spitting stones into a hedge like naughty children, and somehow ended up at a stretch of coast I'd failed to locate on any map.

The water was that impossible turquoise you assume has been Photoshopped until you see it yourself. A handful of locals were swimming, a woman was reading under a striped umbrella, and there was absolutely nowhere to buy an overpriced cappuccino. Rob went in up to his knees and yelped about the temperature, which our daughter found hilarious and I found deeply satisfying.

Later, properly lost now, we stumbled on a bakery where the woman was pulling taralli from an oven that must have been older than me. She didn't speak English, my Italian extends to ordering wine and apologising, but she fed us samples until we bought more than we could reasonably eat and pointed us down another alley that she seemed to suggest would get us somewhere familiar. It didn't, not really, but it got us to a courtyard where someone was practising trumpet badly behind shuttered windows, and then to a vegetable patch where an elderly man was watering his tomatoes in his vest and giving us a thumbs up like we'd planned to visit all along.

By the time we found our way back, the sun was setting and the outdoor shower had gone from "rustic" to "absolutely essential." I stood under it in my swimming costume, watching the sky turn pink over the olive trees, and thought about how I'd spent months planning this trip and the best bits had happened because I'd got everything slightly wrong.

The farmer, the cherries, the trumpet, the tomatoes. None of it was on any list I'd made. I think that's rather the point of places like this. You don't find them properly until you've stopped trying so hard.