The Ride to San Gimignano; One Perfect Day in September

A cyclist riding in Tuscany with the towers of San Gimignano in background

San Gimignano is one of the most beautiful towns in Tuscany. As you crest the nearby hills, its 14 towers rise up like a beacon from the majestic medieval walled town, welcoming us on our Tour of Tuscany finale.

Sunrise in Tuscany

From our villa in the Val d’Orcia, we awake to a pale sunrise trying to break though the mist that shrouds our hill top home, providing just another reminder that the seasons have started to change and we are now well into Autumn.

Our usual routine is now second nature. With our “pro” hours start time and a couple of caffe taken over a leisurely breakfast to ensure we are adequately fuelled for the day, everyone is molto tranquillo.

We say our goodbyes to Silvia and Paolo and then make our way down the gravel path to the gates to start our journey. We know these hills well now, having spent four days here, but today we see them from a different perspective. As the light mist at the top of the hill becomes more dense as we reach the valley floor, the village is all but deserted and in the blink of an eye, we ride from east to west and then out of town

Riding into the fog in Tuscany

The road is straight with a climb at the end, but with the fog we are only able to see a couple of hundred metres at a time. So there’s no time to be concerned with how big, how far or how steep the hill is. There is just a beautiful stillness that everyone absorbs as we all roll through at different points on the road.

A mid ride coffee during a Tuscany cycling holiday

We clear the climb and buckle up for a superb descent that is punctuated with a mid-ride caffe.

The landscape of the Crete Sinese in Tuscany

The terrain dramatically changes form the deep green bosco to a bare brown land that has been recently toiled. The contrast is amazing and spectacular. We see Siena in the distance and keep it at arm’s length as we follow the ebbs and flows of the small rises and short descents, taking the back roads that skirt this majestic town until we leave it behind us.

A little road side Osteria with a big reputation provides us with a panino… think local Tuscan fennel salami with grilled zucchini… buonissimo… and a short spell.

A tuscan gravel road

The empty roads and farmland just keep rolling out before us as small villages come and go, and before long we are climbing again as we ascend from the valley floor, passing through another tiny village with the road cutting through its centre. A twist and a turn and we are at the top, and now just bumping along the ridges in the midst of the vineyards of one of our personal favourite white wines, Vernaccia di San Gimignano.

Post ride beers in Tuscany

From here, the imposing towers of San Gimignano can be seen in the distance. They almost feel close enough to touch but fittingly for our final ride in bella Toscana, we still have one last thrilling descent, followed by a final climb into the cobblestone streets and welcoming arms of a frosty cold Moretti.

After 8 days of riding and a food and wine adventure through the very best of Tuscany, San Gimignano provides the perfect setting for our finale. If you’d like to join us on our Tour of Tuscany in either June or September, visit our tour page for more information.





More Inspiration

Scroll to Top