The trip to Tuscany that lives up to the imagination – and how to retrace it

WT Writer
Sep 6, 2021

Celestial hill towns, heavenly art, food and drink to die for… Pootling about with her friend Chiara (in Chiara’s red Cinquecento), Dana Facaros draws the dream holiday map to Tuscany.

Chiara and Mario were doing it on purpose. It was late September, but still warm enough for aperitivi outside their old farmhouse overlooking the undulating Val d’Orcia — the ultimate Tuscan photo op. Over the long hot summer, the earth had sucked in enough sun to add an inner glow to the black-dagger cypresses and the chalky hills, blurry in the twilight mist.

A decade-old bottle of Brunello filled our glasses as we munched on crusty bread dipped in newly pressed olive oil — Tuscany’s green elixir. Then, for the full Tuscan whack, they put on Callas singing Puccini’s heart-aching Un bel di vedremo from Madam Butterfly. I had to ask: “Come on, do you realise how lucky you are?”

Italian ciabatta bread with olive oil
Italian ciabatta bread with olive oil. Image Credit | Istock

“After 30 years here, we sometimes take it for granted,” Mario said. “We need someone to look at it for us, to see it through fresh eyes.” And then he screeched. “Dio mio! Garibaldi just pooed in your shoe!” It was just as well that their ginger tom cat broke the spell or I might have collapsed from the surfeit of beauty.

There is Italy, and then there is Tuscany, the gold standard by which all other Italian regions, trying to be the next tourist honeypot, measure themselves. But Tuscany is a tough act to follow. First came the arty Etruscans, who taught the Romans everything they knew. Then, already one of the wealthiest regions in medieval Europe, it invented the Renaissance almost single-handedly.

Monticchiello Tuscany Italy
Monticchiello Tuscany, Italy. Image Credit | Istock

But in the 16th century, the money and talent moved to Rome. Tuscany slid into a twilit retirement, leaving much of its incomparable art and architecture, as the Italians say, com’era, dov’era (‘as it was, where it was’). It’s no wonder that I return to the region, not annually, but seasonally, for my fix of beauty.

Of all the many parts in Tuscany where you will be dizzied by its good looks, the hill towns below Siena are the most obvious. Even just a few days here are candy for the soul. Take Pienza, near Chiara and Mario. Nicknamed the ‘ideal city, it was built in the 1460s for humanist pope and local lad Pius II.

Pienza never became the lightning rod for culture that Pius had hoped — today, it’s known best for its sheep’s cheese. It never became a city, either. But the centrepiece, Piazza Pio II, with its dreamy air of unfulfilled expectations, is the perfect stage for the daily lives of Pienza’s 2,000 residents. Waiting for Mario one day, I watched them meeting up for chats in a slow waltz amid the perfectly proportioned Renaissance palazzi and cathedral. Chiara has a theory that Italians subconsciously dress in colours to match the stone of their town. She may be right.

Arezzo, Piazza Grande (Tuscany,Italy)
Piazza Grande, a medieval square in Arezzo. Image Credit | Istock

As we walked through an alleyway, a round wooden cheese mould came hurtling towards us. “Eh, signora! Fai attenzione!” yelled a couple of boys, who were bowling it at a juice packet. I thought it was a game of youthful invention, but it’s called ruzzola, Mario explained. “They’ve been playing it here forever. You can even see Etruscans playing it on a fresco in Tarquinia — only without a juice packet!”

The next day, Chiara and I set off under the blazing sun in her shiny old red Cinquecento. We wound around the cypress-lined lanes that appear on half of Tuscany’s postcards: to San Quirico d’Orcia, 10 minutes southwest, alongside Lycra-clad cyclists and Dutch, French and German pilgrims taking the Via Francigena to Rome. The town’s church of Santi Quirico e Giulitta, with mermaids having a tête-à-tête and scaly fish dragons French kissing over the door, was founded in the 8th century, about the same time as the road itself.

Pilgrims on the way to Rome looked forward to soaking in the waters at bijou Bagno Vignoni. Today, the steaming ancient pool, where St Catherine of Siena and Lorenzo de’ Medici once dipped, takes the place of a piazza, embraced by Renaissance buildings. Although it’s been closed for a few years, others are open; Chiara and I happily wallowed in the Albergo Posta Marcucci’s, with priceless views over the hills.

Yellow scooter in tuscan Cortona town
Scooter parked up in Cortona town. Image Credit | Istock

Prune-fingered, we carried on to Montalcino, another hill town on the Via Francigena. It was the time of the vendemmia and at a hillside vineyard, we watched the workers bring in crates of glistening blue-black bunches, destined to become the divino Brunello.

Heading back to Pienza, we stopped for an espresso in a roadside cafe. “Look at him,” Chiara whispered mysteriously when the barista was out of earshot. Bright eyes, thin face and lips, receding hairline — I drew a blank until she thrust her phone at me. “Machiavelli! A dead ringer!” she laughed. ‘It’s funny how many Tuscan throwbacks you find. Once, in the toll booth on the autostrada near Lucca, there was a Botticelli angel! The most beautiful man I’d ever seen.”

View on Tuscan landscape from small church on a hill.
Hilltop view of the Tuscan hills. Image Credit | Istock

Early the next morning, mist still lingered in the hills as we headed east to Cortona. Piled high on a natural balcony, with mesmerising views over the Valdichiana’s rolling landscape, Cortona is a bold sight. According to Virgil, it’s as old as the hills it perches on, too — one of its pioneer citizens is said to have founded Troy. The Museo dell’Accademia Etrusca is home to treasures including a round Madonna and Saints by Cortona native Luca Signorelli, in which a gentle St Michael shows the baby Jesus his soul-weighing scales as if it were a toy.

Chiara preferred the bronze statuettes of the Etruscan gods Selvans and Culsans: naked except for their boots, androgynous, ringletted hair and a provocative hand on hip — exactly like Donatello’s scandalous David, which takes pride of place in Florence. “Do you think Donatello ever saw these?” I asked.

“I doubt it! I think the David may have been the most mysterious Renaissance throwback of them all.” Tuscany is full of surprises.

Beautiful sunrise in Tuscany, Val d'Orcia
Beautiful sunrise in Tuscany, Val d’Orci. Image Credit | Istock

It also has the best cows. En route to Arezzo, we came upon a dozen white Chianina — bovine royalty — placidly chewing the cud in a field. We unwrapped porchetta sandwiches that we’d bought earlier from a roadside van — slow-roasted and herby between slabs of Tuscany’s dry, salt-free bread — and chewed back at them. They were magnificent beasts, towering over us — the oldest, biggest and heaviest breed in the world, prized in ancient times for pulling ploughs and as sacrifices to the gods. Now most end up as bistecca alla Fiorentina.

Arezzo is one of Tuscany’s less-visited art cities, having gifted the world the poet Petrarch and Guido d’Arezzo inventor of musical notation. Most visitors come for Piero della Francesca’s sublime 15th-century fresco cycle The Legend of the True Cross in the church of San Francesco. As a former resident, I would go there often to gaze at his great battle scenes and the transcendent Dream of Constantine, in which the pagan Roman emperor is visited by an angel who will spark his conversion to Christianity. Restoration of the frescoes was completed 20 years ago and they look as if they were painted yesterday: clear, vibrant and filled with the timeless stillness that’s the trademark of Piero, who was obsessed with clinical lines and perspective. They have, I thought while gazing at them, that Tuscan je ne sais quoi.

On my last evening, Mario, Chiara and I sat outside again, watching the sun sink behind Italy’s most famous backdrop. Clouds sent dark shadows rollercoasting over the hills; the olives trembled silver in the breeze. “If Tuscany had been as flat as Kansas, would it have produced such great artists?” I wondered.

Tuscan hills at sunset.
Tuscan hills at sunset. Image Credit | Istock

“But not all Tuscan landscapes are natural,” Mario said thoughtfully. “Back in the days of the Black Death, when the elite escaped into the country and started turning castles into villas, they wanted to make the countryside as beautiful as their frescoes. So the countryside is like a painting, I guess — a 14th-century moment frozen in time.”

We fell silent as the evening deepened and Venus hovered into view next to the slimmest of crescent moons. “Oh, go on then,” I said. “Put on some Puccini.”

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