Travel

// Driving through Tuscany

Picture the scene. It’s a beautiful, breezy summer’s day – You driving along a deserted road, getting lost between the vast Italian wine lands, you singing along to your favourite song as the golden sun warms your bare arms, your hair’s blowing in the wind and you cruising along the open road without a care in your world. That feeling of pure happiness and freedom is a moment you wish you could hold onto forever. You can sense the stillness all around you. Everything feels calm and your mind is completely at ease…

This was me. Driving alone and getting lost, both literal and figural, between the valleys and peaceful roads of the Tuscany region. Let me share my story with you, of the time I threw caution to the wind, rented a car on a reckless whim and went for one hell of a ride!

I should start by telling you that I had freshly turned the earth-shattering ripe ‘ole age of Thirty. As you may, or may not know, this really does something to a girl. It brews, stirs, and well lingers even if you asked for it or not. I was currently on a solo Eat. Pray. Love journey backpacking my way through Europe. My highly anticipated, or should I say dreaded age-of-realization, birthday came and went without much enthusiasm. It was at this ‘lingering’ phase that I chose to live out my very own movie moment. I clearly spent my youthful Twenties watching waaay too many self-discovery movies. It was a Tuesday afternoon, and I was sitting at a café in Florence, playing out the worn out tale of trying to figure out how to grasp this new chapter of my life, when all I really wanted to do was to drink a glass of wine, roll over and take a nap. I sat there, and channelled Diane Lane from ‘Under the Tuscan Sun’. Oh Yes. Yes, I diiid! It was right at this moment that I decided that myself and my already strained travel budget was going to rent a car and drive through Tuscany.

It seemed like a perfectly simple idea. My bags and my defiant self-walked to a well-known car rental agency in the centre of Florence. I sat in the waiting area intently listening for my assigned number to be called out and silently prayed that they would give me a car sans International Drivers License. I told you, I was defiant. I smiled, remained positive and manifested that open road, hair blowing, music blaring, sun-kissed version of me, like nobody’s business. When they presented my car to me and handed over the keys, I jumped inside, turned on the engine, and shamelessly squealed and high fived myself. I laughed out loud to myself as I thought that, I had indeed got my Italian Stallion, after all. Yes, my very own navy suited up Italian Stallion. I had no Wi-Fi, no GPS, but a whole lot of untouched road ahead of me which required my undivided attention, and I was going to give it just that.

The incredible thing about renting a car is the freedom it allows you to be completely spontaneous. It also gives you a sense of stability, as all your possessions are constantly with you, and you know that if all else fails, there’s a roof over your head. You get to see and discover a whole lot more when compare to only traveling via bus or plane to more easily accessible cities. I drove with no real destination in mind. I had a vague game plan of eventually making my way to Sienna. How and when I got there was entirely due to the mood I was feeling, at the time. It felt so free and liberating to drive again. Once I got over the whole ‘driving on the opposite side of the road in a strange car’ realisation, life was pretty damn great! I spent my first 30 minutes chanting, “Keep Right, Keep Right, you best keep RIGHT!” repeatedly until it felt slightly normal. The first day was spent passing through small towns, which seemed to appear out of nowhere, as I got swept up in all the endless sweeping green hills. I arrived in a medieval town called, Colle di Val d’Elsa, just as the was sun setting. I carefully parked the Stallion, patted him proudly on the bonnet and proceeded to walk down little alleys searching for a home for the night. In broken Italian and plenty of hand gestures, I booked the cheapest available room. That night, I fell into a deep, peaceful sleep feeling perfectly content with the start of my adventure.

The remainder of my 5-day road trip through the vast Chianti region was spent pulling off at any cute picturesque towns, that caught my attention. I occasionally stopped and drank a glass of fruity wine from farms, whose name’s appealed to me simply for being unpronounceable and romantic sounding in the slightest. Following a recommendation from a friendly old Italian woman who was fascinated by my journey, urged me to visit Monteriggioni. I am so glad I did! Monteriggioni is a tiny medieval, walled Town. No cars are allowed in, which meant my Stallion could sit back and relax. The little town was like stepping temporarily stepping back in time. Taking in its fascinating history, old charms, cosy alleys, and peacefulness, it was unlike anything I had seen. The view of the Tuscan countryside from it’s surrounding walls was breathtaking,

There were countless moments while driving I would pull to the side of the road to completely take in the surroundings. I reflected on all the stumbles, laughs in my life that had led me to those hilltops. I took in its various textures, colours, smells, and its stillness and comforting effects. It was one of those thrilling ‘pinch, me, I am not dreaming’ moments. I can’t tell you the number of times I got lost, the free offline map app I was relying on didn’t fair to well deep in the countryside. But, then again, isn’t that part of the magic of travelling. You never really lost, but merely taking a different route.


If you ever heading to Italy, seeking a calmer pace, nature, and the allure of being completely alone with your own thoughts, I strongly urge you to hire a car and drive through Tuscany. It was a beautiful, wholesome experience, one that I reflect proudly back on.

It’s also just pretty damn cool to enjoy that feeling of your hair blowing in the Tuscan breeze…

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Need a place to stay? I recommend the following places for their originality and beautiful setting.

Hotel del Lago, Cavriglia
Bassetto Guesthouse, Certaldo

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