Vintage Wheels and Wine: A Fiat 500 Tour of Chianti


Last month, I was lucky enough to spend some time in Tuscany, exploring its countryside and coast. While I was there, I spent a day travelling around the Chianti hills in a vintage Fiat 500. I asked one of my travelling companions, Sarah, to write a post about our trip – here’s her account…

Peep-peep-peep-peep-peeep bounced off the 800-year-old exterior walls of Monteriggioni. Then there was a peep-pee-pe-pe-peeep from the other car, a gentle roar of the engines and we were off, chugging down the hillside and cutting a path through the Tuscan countryside once more.

We were on the last leg of our vintage Fiat 500 tour of Chianti, one of Italy’s most popular wine regions, in one of its most famous cars.

It was a day of classics. The original Fiat 500 is a classic car – I’m not referring to those roomy young upstarts with hefty 1.1 litre engines. It was manufactured between 1957 and 1970, measured just 2.97 metres long, and was powered by a 479cc two-cylinder, air-cooled engine.

We had two for our tour group – a cherry-red one, the youngster at just 45 years old, and an old lady navy car, which was first let loose on Italy’s roads in 1968.

Vintage Fiat 500s in Chianti

As we clambered inside there were more than a few reminders of just how much cars have changed over the years. The Fiat 500’s engine is in the rear, so the ‘boot’ was instead at the front of the car and had just enough space for the spare wheel and a handbag or two. A good job, as the interior of the car was only big enough to comfortably fit three passengers – two in the back and one in the front, plus our driver and guide, Ciro.

These cars were free of the fancy bells and whistles you find now. The dashboard was simple with a speedometer and temperature gauge. The roof was fabric, and as the sun broke through the early cloud of the day we took it down, turning our little Fiat into a convertible. However that inimitable Italian style was trumped by function in these grand dames of Italy’s roads. The fabric roof, I discovered some weeks later when this motoring icon was featured on the BBC’s James May’s Cars of the People, kept the Fiat 500 light and lithe by reducing the amount of sheet metal used.

By today’s standards, however, these old beauties aren’t light and lithe enough to travel very far, or very fast – they had a top speed of around 50 kilometres per hour. But what they lacked in speed and motoring pizazz, they more than made up for in style and fun.

“Fantastico!” enthused a wide-eyed man as we parked in Castellina in Chianti. He continued with many other Italian superlatives I didn’t fully understand, but knew from his impassioned reaction that it brought back all kinds of memories for him.

Chianti hills Tuscany where they drove through in the Vintage Fiat 500's

And in many respects our tour was a journey into Tuscany’s past, exploring this most famous of wine regions, from its endless vines, to the towns that crowned its hills.

Take Castellina in Chianti for example – there we ambled the medieval street of Via Delle Volte, which forms an underground tunnel around the town, and was used in its protection from invaders. Then there was its 14th-century castle – Castellina means small castle after all – which has great views over the surrounding countryside.

We also unearthed the legend of the black rooster – the logo and trademark of real Chianti Classico – the premium wine produced traditionally in the region. It dates back the 13th century, when it was drawn on the banners of the Chianti League, the military and administrative institution. But it is also linked to the on-going conflict between the two republics of Florence and Siena. Tired of the constant battles to define territories in Chianti, they agreed to settle the dispute with a contest. A knight would leave each city in the morning at the crowing of a cock. The Florentine knight would head towards Siena, the Sienese’s towards Florence. At the exact point where the two met, they would seal the border.

The Florentines entrusted their wake up call to a black rooster, which they’d kept hungry the night before. The Sienese chose a tame white rooster, which had been satisfied by a hearty evening meal. The hungry Florentine rooster woke his knight earlier and he was able to annex a larger portion of Chianti for Florence.

Leaving Castellina in Chianti full on history, but hungry for wine and great Tuscan food, we headed to Poggio Amoreli.

Poggio Amoreli Chianti wine

The vineyard is one of the many producers of Chianti Classico in the region. There we feasted on a lunch including antipasti of Italian hams and meats and a variety of home-made pasta dishes. All were served with wines from their vineyard – a 2013 Vermentino, a 2009 Brunello di Montalcino, and of course their Chianti Classico (2013).

After lunch we were off once more. Pootling through the countryside, the roof down to let our hair blow in the gentle wind we drove under blue skies, the occasional cloud puffing by with each bend in the road. Vines twisted their way across the countryside in neat patterns and the sunlight created the sublime views for which Tuscany has become so famous.

Reaching the outskirts of Monteriggioni, we wound our way up the hillside, the little Fiats showing steely determination to make it to the summit. Parking outside the town’s aged walls we walked in to discover more about it.

Another medieval town, Ciro and his colleague Dario took us through its important role in the conflict between Siena and Florence (it is today in the Sienese commune of Tuscany), and interesting tales of this great walled town.

Santa Maria Assunta, Chianti

Sitting in its main square, Piazza Roma, I breathed in its history, one set in motion in the Middle Ages. It seeped through its thick outer walls, traced a path along every potted grey stone in every building, like the Romanesque church of Santa Maria Assunta and the small restaurants serving traditional, hearty Tuscan dishes.

Before leaving town I popped into a delicatessen, leaving moments later with enough local meats, cheeses and, of course, Chianti, to weigh down our little Fiat.

But the cars didn’t struggle – we drove downhill all the way, until Monteriggioni’s fortress walls were a distant speck.

Tootling back home we arrived at the Fiat garage to an engine-roaring finish with horns peeping their peppy sounds, their chirpiness a refection of our fun-filled day in the Chianti Hills.

Vintage Fiat 500 tour of Chianti

Sarah Lee is founder and editor of LiveShareTravel, an award-winning luxury travel blog dedicated to liberating luxury for smart travellers. She’s passionate about seeking out the best in luxury – from great hotels to real experiences that make travel the best thing money can buy.

Take a look at Sarah’s video of her Chianti tour above.

Fancy your own Chianti road trip? Take a look at our holidays to Tuscany.