Asciano to Montalcino, my favourite day in Tuscany
The second in a series where I write about my favourite day on each of our tours.

My favourite day on our Tuscany tour takes us through Le Crete, on Thursday, as we make our way from Asciano to Montalcino, visiting the Abbey di Monte Oliveto Maggiore on the way. Here’s the route in detail.
Don’t forget, you can click on each photo to see a larger image. Most of these photos were taken by Chris Yates – thanks Chris.
From Asciano to the Abbey is just 10 Km – all uphill, as plenty of Chain Gangers will testify! Quite gentle, but it still takes us over an hour, and as the monks at the Abbey throw us out at midday, we try for an early start from Asciano.
1. The Abbey di Monte Oliveto Maggiore.
This is still a working monastery. You pays your money to a monk at the cash desk, you buy your guide book in the gift shop from a monk, and it’s a monk who makes us all take a little brown skirt to wrap around our cycle shorts. The attraction is a fresco cycle that stretches all the way round the cloister highlighting scenes from the life of St Benedict.
St Benedict was a very significant figure in the early part of the 6th Century. Some Saints became saints by claiming to have witnessed the truth of the transubstantiation in a dream – there you go son, become a Saint. Good dream. Others are about to become saints for turning a blind eye to the Holocaust (OK, slightly controversial, but Pius XII didn’t do a fat lot!). But Benedict did stuff, and if you’re European, he’s your patron saint. The Rule of St Benedict, including modesty and work, was the source of the monastic code for all Orders, the Benedictines, the Cistercians, the Franciscans , and his base was his famous abbey, the enormous Monte Csssino between Rome and Naples.
I’m conscious I’m not selling these frescoes very well – they’re fantastic, and you can see some of them in Chris Yates’s collection of photos here. Alternatively, you can read more about the Abbey on Wikipedia here.
2. Brunello di Montalcino
Having cycled 10 Km up to the Abbey, we cycle 10 Km down to lunch in the medieval town of Buonconvento. Last October I tried to cycle all the way from the Abbey to Buonconvento without pedalling. Turns out it’s not all downhill, but bloody nearly. The Mayor of London, Boris Johnson, used the phrase ‘windblown bliss’ talking about his love of cycling. That’s this stretch.
After lunch we head for Montalcino. This is a beautiful medieval hilltop town, sitting 567 metres above sea level overlooking the Val D’Orcia. Montalcino is best-known for its famous wines, the Brunello di Montalcino. Every third shop in the town is an enoteca, a wine shop, and on our climb up into the town we visit the vineyard of Tenimenti Angelini, producers of the famous Val di Suga, among other prestigious wines.
I’ve no idea why they let us visit here. Each year when I call they tell me “we don’t accept visitors in the afternoon. Wait, are you the cyclists? Oh, will we see you at 3 o’clock as usual?” One day they might not say yes, but until then it’s a privilege for a wine-lover to visit this vineyard.
2. Montalcino
Montalcino was part of the Sienese sphere throughout the renaisaance period, which placed it at odds with Florence in the seemingly endless wars between the Ghibellines (supporters of the Holy Roman Empire) and the Guelphs (supporters of the Papacy). (If you want to read a brilliant book about how the fall of the Roman empire led directly to the mosaic that was renaissance Italy, to Unification, and even why Italy is the way it is today, then have a look at “ The Italians.” by John Hooper. Just order it, it’s brilliant.)
If you want to see more photos of our tours in Tuscany, here are three galleries you might enjoy: