Driving Adventures/Fails in Tuscany

Driving adventures in Tuscany

I am not an overly curious person, nor am I the bravest of drivers. Put those two traits together, and you get someone who, when behind the wheel, sticks religiously to the roads they know. It’s a strategy that has served me well for the most part, though not without a few memorable misadventures.

In my early days of living in Tuscany – 16 years ago now – I managed to get my car stuck twice. The first mishap happened when I mistook a glistening country lane for something enchanting—completely missing the fact that those “lovely sparkles” were actually ice. If I’d been a bit more curious, I might have taken a closer look and spared myself a stressful driving ordeal. Instead, I found myself sliding on a steep, narrow bend, forced into a nerve-wracking eight-point turn that felt like it shaved years off my life. The second time, a few years later, I attempted to take a “shortcut” across a field rather than risk a mildly tricky driveway leading to a friends house. That field turned out to be a bog. Not only did I need to be towed out, but I also discovered – at the worst possible moment – that my car didn’t have a tow bar.

Fast forward a decade, and I had developed a foolproof driving strategy: check Google Maps, get extra verbal directions, and, most crucially, stick to the routes I know. This approach had worked brilliantly – until a few weeks ago.

I was showing a lovely farmhouse in the countryside to a couple who were looking for at property in the area. After touring the house and grounds, they turned to me and asked the fatal question, “What’s further down the road?”

“No idea,” I admitted. Despite having visited the property many times, I had never ventured beyond its familiar confines.

“Let’s go see!” they suggested enthusiastically.

My gut instinct screamed that this was a bad idea. It was a dirt track. Dirt tracks in Tuscany can be deceiving – sometimes picturesque, sometimes the setting for a vehicular horror story. I should have listened to my gut. But that morning, caught up in their sense of adventure, I thought: why not?

A few minutes later, we were rolling down the track. Almost immediately, I realised my mistake. The road was muddier than I had anticipated. We reached the bottom, got out, and took a look around. There was, unfortunately, nothing of particular interest—mostly mud and brambles that did nothing to inspire a newfound curiosity in me.

Time to head back up.

I put the car into gear, pressed the accelerator… and we made it almost to the top before the wheels started spinning. And then—nothing. We were stuck. I tried rolling back down to get a better start. No luck. I tried again. And again. The hill was winning.

Turning to my trusted Google Maps strategy, I looked for an alternative route. The app suggested a “road” that, upon closer inspection, turned out to be a barely visible track leading directly into a lake. Not exactly helpful.

At this point, I discovered that my two clients were, in fact, a power duo of problem-solving. One was ex-military; the other, a pilot. Without missing a beat, they sprang into action. While I hiked up the track in search of help, they got to work, digging out the mud from the tyres and fitting the snow chains I had with me (a legal requirement in Italy). By the time I returned, expecting to strategize a dramatic rescue operation, the car was already back at the top of the hill, and my clients were standing there, cool as ever, as if this was just another Tuesday.

A bit muddier, slightly wiser, and with a great story to tell, we drove away—me with a reinforced commitment to my rule: always, always stick to the roads I know.

(And maybe listen to my gut next time)

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