I should have known the holiday was going to be interesting when I managed to get my rucksack strap caught in the hire car door at Catania Airport. There I was, frantically waving at my partner to stop driving while being dragged along the tarmac like a particularly enthusiastic water skiier. Not my finest moment, and certainly not the relaxed Sicilian arrival I'd pictured.

By the time we actually reached our holiday home in Siracusa, I was already half-melted and sporting a impressive graze on my elbow. The property sat tucked away in a quiet residential corner, the sort of place you'd never stumble across unless you were specifically looking for it, or in our case, following Google Maps with the desperate faith of someone navigating by starlight. A cream-coloured villa with terracotta roof tiles and shutters that had seen better decades, it looked exactly like the kind of place where nothing much happens, and everything happens, all at once.

We dumped our bags and did what any sensible person does after a near-death experience with a Fiat Panda: we went for a wander with absolutely no plan whatsoever. This, as it turned out, was the best decision we made all week.

Siracusa's old town, Ortigia, gets all the guidebook love, and fairly enough, it's gorgeous. But we were staying on the mainland, in that slightly scruffy, lived-in zone where actual Siracusans actually live. Within ten minutes of leaving our front door, we were properly lost. Not charming-lost, not "oh look at this picturesque alley" lost. Genuinely, "I think that dog is following us and I don't recognise that graffiti" lost. My partner had the map. I had the sun cream. Neither of us had a functioning sense of direction.

That's when we found the bar. Not a bar-bar, mind you. A hole-in-the-wall place where an ancient gentleman was serving granita from a machine that looked older than he was. Lemon, naturally, because this is Sicily and anything else would be borderline offensive. He didn't speak English. Our Italian extends to ordering wine and apologising. We managed both, extensively. The granita was the best I've ever tasted, served in a plastic cup with a spoon that had definitely been through someone's dishwasher approximately four thousand times. We sat on a wall opposite a garage where three men were having what appeared to be an extremely heated discussion about football, or possibly politics, or possibly both, which in Italy amounts to the same thing.

The getting lost continued. A left turn that should have been a right took us past a courtyard where someone was drying octopus on a clothesline, which is not something you see in Surrey, let me tell you. Another wrong turning deposited us in front of a church that wasn't in any guidebook, where an elderly woman was arranging flowers with the precision of a bomb disposal expert and the solemnity of a state funeral. She let us in. We stayed for ten minutes of complete silence, broken only by my stomach rumbling embarrassingly loudly after all that lemon ice.

By evening, we found ourselves down near the water, not the fancy marina but the working bit, where fishermen were mending nets and complaining about the price of diesel in voices that carried across the harbour. Someone offered us wine from a plastic bottle. We accepted, because holiday rules apply, and because refusing seemed churlish when we'd already accepted so much accidental hospitality.

Walking back in the dark, still not entirely sure of our route, I realised something. I'd spent months planning this trip, cross-referencing reviews, bookmarking restaurants, mapping optimal routes. And the best moments, every single one of them, had come from being gloriously, stupidly, wonderfully lost. There's a metaphor in there somewhere, probably something about life journeys and embracing uncertainty, but I'll spare us both the therapy session. What I will say is this: if you find yourself in Siracusa with no particular place to go, keep walking. Take the turn that looks less promising. Follow the dog, within reason. The Sicily that exists between the recommended attractions, the one you have to earn through poor navigation and excessive optimism, is the one that stays with you.

We finally made it back to the villa after dark, still laughing about my airport drag-racing debut. The next morning, we set out again with no map and no plan, which is either the definition of insanity or the beginning of wisdom. In Sicily, I'm fairly certain it's both.