Italy - part 2: How to Have a Bad Day in Tuscany: A Masterclass

For most of us, the art of having a bad day requires no formal training. Life has already provided a generous curriculum. But for those rare individuals who have floated through existence in a state of uninterrupted bliss, I offer this journal entry as a public service. A syllabus. A field guide. A cautionary tale. Welcome to Day Four of my Italian adventure — a day so educational it should count as continuing professional development.

Lesson 1: Trust No Nurse With a Clipboard

Where I learn that milk is apparently a controlled substance

I awoke from a pleasant dream, stretched luxuriously in my hotel bed, and descended to breakfast feeling invigorated. This optimism lasted approximately four minutes — the time it took for the Sugar Nurse’s dietary regime to reassert itself in my consciousness.

I sat before my yoghurt and granola (both approved), reflecting on the moment I had proudly told her I ate “healthy fruit and fibre cereal” at home.

“With milk?” she’d asked.

“Yes, semi‑skimmed.”

“Milk turns to sugar,” she’d declared, with the solemnity of a judge handing down a life sentence. “No more milk”. Awkward.

I nodded politely, the way one does when confronted with a zealot, and quietly mourned the concept of breakfast as I once knew it, and crunched my nuts and seeds.

Lesson 2: Rain Is Just God’s Way of Testing Your Optimism

Where the weather begins its slow, methodical assault

The route to Val d’Orcia looked simple: 90 minutes, a few villages, a supermarket stop. Easy.

The weather disagreed.

By the time I reached San Quirico d’Orcia, the rain had escalated from “light drizzle” to “biblical reckoning.” I rewarded myself with a croissant and a latte — which I must have mispronounced, because I was handed a double espresso instead. Clearly divine intervention was still in effect.

Shopping done, I sprinted through the downpour to the car, soaked to the bone, and set off on the final leg.

Lesson 3: Never Follow a Sat‑Nav Down a Road That Looks Like Custard

Where the Fiat 600 attempts to become a pottery wheel

Fifteen minutes from my destination, the sat‑nav instructed me to turn left. The “road” it led me onto was made of saturated, bright yellow clay — the sort of material that would delight a potter but is less ideal for driving.

The car couldn’t decide whether to sink or spin. I feathered the accelerator with the sort of patience normally reserved for bomb disposal technicians.

Then came the farm track: steep, flooded, gravel loosely sprinkled over clay like a token gesture. The windscreen wipers flailed at maximum speed, performing interpretive semaphore. Water streamed down the slope. The Fiat lurched, slipped, and clawed its way upward with all the enthusiasm of a cat being asked to take a bath.

At the final incline — the steepest, naturally — the tyres spun helplessly. My fingernails dug into the steering wheel. My buttocks clenched with such ferocity that I’m fairly sure I briefly achieved lift‑off.

And then — miracle — I reached the top.

Lesson 4: When in Doubt, Your Accommodation Is Always the One Without a Number

Where I wander a hamlet like a drenched, confused postman

The rental company’s instructions were simple:

“Find house number 18. Drive past it. Look for a gate.”

That was it.

The hamlet I arrived in was utterly deserted. Not a light in a window, not a voice, not even the distant bark of a dog. Every house looked shuttered, silent, and vaguely judgemental. There was no one to ask, no neighbour to wave down, no kindly old man to point me in the right direction. Just me, the rain, and a growing sense that Tuscany had decided to test my emotional fortitude.

I drove back and forth through the tiny cluster of houses, failing repeatedly to locate anything resembling my accommodation. I called the rental company. No answer. Signal intermittent. Internet nonexistent. My optimism was dissolving like sugar in forbidden tea.

Lesson 4½: Never Assume a House Is Yours Just Because It Has a Number

Where I accidentally terrorise an innocent Tuscan household

Eventually, I identified what I thought must be house number 18 — the only number mentioned in the instructions. Desperate and drenched, I set about trying to locate the key safe. The instructions mentioned about a path to the left, look for a tree (there was an entire wood), behind a wall, opposite a garden etc. Basically, walk in any direction you want.

This involved a series of increasingly undignified manoeuvres: shaking decorative wooden boxes, kicking suspicious stones, and peering behind plant pots with the intensity of a man searching for buried treasure. I even pressed my face against a window, hoping for clues inside.

Instead, I was greeted by the warm glow of interior lights — a detail I had somehow failed to notice earlier.

A creeping dread washed over me.

If the lights were on, someone was almost certainly in the house. And if someone was in the house, then they were probably watching, from behind a sofa or a curtain, as a lunatic in a waterproof jacket stormed around their property in the lashing rain, rattling objects and muttering to himself. Indeed, the scene was grim and incriminating.

It was only then, soaked, panting, and morally defeated, that I realised my mistake: this was not my accommodation. I had spent ten minutes conducting a one‑man search‑and‑seizure operation on a completely innocent Tuscan home.

I retreated into the darkness with the quiet shame of a man who has just traumatised a family of strangers - whom, it would transpire, would be my neighbours for the week. Awkward.

Lesson 5: Olive Oil Is Not a Moisturiser

Where I accidentally baste myself like a Christmas turkey

Inside my actual accommodation — eventually located after further wandering — things deteriorated quickly.

I couldn’t find an oven. The coffee‑making facilities appeared to predate the Renaissance. And when I attempted to cook my Tuscan beef recipe, the flimsy olive oil bottle collapsed as I pressed the cap on, erupting like Vesuvius and covering me from head to toe.

I didn’t even swear. I simply stood there, shimmering gently, and accepted my fate.

Too tired to change clothes, I cooked while skating across the kitchen floor like a budget Torvill and Dean. My left eye still shimmers from freshly pressed virgin olive oil.

Lesson 6: A Fireplace Without Kindling Is Just a Decorative Hole

Where I attempt to ignite hardwood using notebook paper and sheer willpower

The rental company had promised plenty of firewood, and they had delivered: huge, dense, seasoned logs. Perfect.

Except there was no kindling. And no matches.

Another 30 minutes of ransacking the house ensued. I eventually found a lighter hidden at the back of a drawer, presumably placed there by someone who enjoyed watching tourists suffer.

With no kindling, I resorted to tearing up my notebook and ripping apart cardboard boxes. I knelt at the fireplace, huffing, puffing, coaxing, rearranging, whispering sweet nothings to the logs. It was like a bizarre combination of courtship and chess.

Finally — a spark. A flame. A tiny victory.

Lesson 7: Always Check the Chimney Vent Before You Smoke Out the Entire House

Where I nearly hotbox myself to death with my own fire

Thirty minutes later, my eyes were stinging. My throat was dry. I looked up.

The house was full of smoke.

I didn’t leap up in alarm. I simply sighed — deeply, from the soul — and opened the windows like a man airing out his own poor life choices.

Only then did I notice a small metal chain beside the fireplace. I pulled it. Something flapped high above. A vent. Of course.

Final Lesson: Tuscany Is Beautiful, But She Will Break You First

Where I reflect on the day’s chaos with a thousand‑yard stare and a glass of red

I raised my glass of Tuscan red, stared into the smoky middle distance, and accepted that the region had chosen to educate me in its own special way.

And that, dear reader, is how you have a bad day in Tuscany. A masterclass in misfortune. A symphony of chaos. A farce so complete that even the Sugar Nurse would have allowed me a biscuit.