I should have known the holiday proper had begun when I got us lost before we'd even arrived. We'd flown into Ancona and collected our hire car, a Fiat 500 that felt more like a sturdy toaster on wheels, and I'd been so smug about my navigational skills. "Don't worry," I'd told my partner, waving my phone about, "I've got this." Two hours later we were on a gravel track that seemed to be leading us into someone's olive grove, with the sat nav cheerfully announcing we'd reached our destination. We hadn't. A farmer in a battered Land Rover eventually pointed us back toward civilisation, or what passes for it in the Sibillini foothills, and we finally crawled up to our Montefortino property as the afternoon light was turning everything golden and slightly apologetic.

The house sat there like it had been waiting for us to get our act together. Stone walls the colour of honey, shutters that had clearly seen better centuries, and a view that made me forget I'd just spent forty minutes reversing down a track barely wide enough for a determined cat. We dumped our bags and stood on the terrace, and I realised something I hadn't expected: the getting lost was already the best part.

Montefortino itself, when we eventually wandered down the following morning, confirmed this suspicion. We'd meant to find the main piazza, obviously. We'd studied the map. Instead we took a wrong turning almost immediately and found ourselves in a narrow vicolo where an elderly gentleman was sat outside his door, shelling broad beans with the kind of patient rhythm that made me want to slow my entire life down. He didn't speak English, we didn't speak Italian beyond the restaurant basics, but he insisted we try some pecorino from a wheel in his cool cellar. It was the sharpest, most alive cheese I'd ever tasted, and we'd stumbled upon it because I couldn't tell left from right without coffee.

That set the pattern for the week. We abandoned any serious plans after day two. A drive meant for the supposedly well-known Gola dell'Infernaccio, which we'd read about in a guidebook, went wrong when I missed a turning and we ended up on a ridge road that petered out above a valley no one seemed to have named. We parked where the tarmac surrendered to grass and walked anyway, finding a chapel so small it couldn't have held more than six people, its door unlocked, its interior smelling of cold stone and old wax. Someone had left fresh wildflowers in a jar. There was no sign, no information board, no coach parking. Just a place that existed because it needed to.

The same thing happened with eating. We'd intended to have one proper restaurant meal, something recommended, something verified. Instead we kept finding ourselves in villages that weren't in our guidebook at all, places like Sefro or somewhere near it, I'm still not entirely sure, where the only open door was a tiny bar with a few tables and a chalkboard menu that changed depending on what the owner's cousin had brought from their farm. We ate truffles we'd watched being shaved at the table, pasta with sauces that tasted of the particular valley they came from, and house wine that cost less than bottled water back home and made me embarrassingly emotional about limestone terroir.

My partner found this all hilarious, of course. I'd been the one who planned our usual holidays down to the nearest toilet stop, and here I was, the architect of our glorious disorientation. By day four I stopped even pretending to navigate properly. We'd head out with a vague direction and see what the roads decided. The Sibillini foothills are generous with their secrets if you let them surprise you. We found a waterfall by following the sound of it through woodland, not a path marker in sight. We discovered a shepherd's shelter converted into the most basic imaginable refuge, where you could buy rough wine and bread and cheese and sit on a bench watching clouds move across mountains that looked painted.

The Montefortino property itself became part of this accidental philosophy. We'd sit on that terrace in the evenings, watching swallows dart about, and realise we'd done almost nothing we'd intended and everything that mattered. The house had no airs, no pretension. The kitchen was slightly wonky, the hot water took its time, and the Wi-Fi worked best if you stood near the northeast corner of the garden with your arm raised like you were hailing a bus. It felt like borrowing someone's life for a week, not renting a polished experience.

On our final morning, I got us lost one last time trying to find the road back to Ancona. We ended up in a hamlet I cannot name, where an old woman was hanging laundry and a dog slept in the only patch of sunlight. We stopped for coffee at a bar that also sold hardware and lottery tickets, and the barman drew us a map on a napkin that turned out to be more reliable than any technology. I kept that napkin. It's creased and coffee-stained and I can't entirely read it anymore, but it reminds me that my best holiday moment was probably the wrong turn that started everything, the olive grove, the farmer's patient directions, the slow realisation that I didn't need to know where I was going to end up exactly where I needed to be.