Trans Tuscany

The magnificent, walled mountaintop town of Volterra is the main highlight of today’s ride.

To get to Volterra you’ll head into some rugged terrain in the beautifully remote region of Tuscany between Castagno and Villamagna. At the 40km (25 miles) mark you’ll see the medieval walls of Volterra perched high on the hill above you, signalling the start of the steep 5km (3 miles) climb from the valley floor to the town gates. Ride through the town gate into the medieval town and stop at one of the magnificent plazas for a coffee or a gelato (or both!).

From Volterra enjoy the sweeping descents, then a wonderful ride through the Castelvecchio Natural Reserve back to the hotel in San Gimignano.

From the famous white wine Vernaccia vineyards around San Gimignano today’s ride takes you into the famous red wine vineyards of Chianti.

Leaving your hotel in San Gimignano, you’ll head east through the Val d’Elsa and Val di Pesa. The bridge over the Pesa river in Bargino marks the start of the long climb to the world-famous Chianti region. The climb tops out in Castellina in Chianti and from there the road rolls through the typical Tuscan oak forests before reaching your hotel in Radda in Chianti.

A magnificent ride around the Chianti hills today.

The ride starts with a wonderful descent through the vast vineyards that surround Radda then continues with a series of short climbs and descents to Greve in Chianti. In Greve you’ll start the 6km (4 miles) climb to Sugame, the first of 3 climbs that come in quick succession. On the climbs, don’t forget to admire the Tuscan olive groves that share the scenery along with the typical vineyards and oak forests. The final climb tops out in Badia Coltibuono before the wonderfully scenic descent back to Radda.

Our destination today is the small hilltop town of Pienza in the Val d’Orcia. Pienza is a magnificent small medieval town with stunning views looking off to the south of Tuscany and the Monte Amiata mountains.

We’re in Eroica territory today so we thought we’d give you the opportunity to take on one of the first strada bianca sections of the famous race, the climb to the Castello di Brolio. From Brolio you’ll jump back onto asphalt and ride through the Crete Senesi to Asciano, with the quintessential Tuscan landscapes of rolling hills and lines of cypress trees leading to hilltop farms. In Asciano the landscape changes as we enter the vineyards of the Val d’Orica, and the small road becomes a complete roller-coaster of short, steep climbs and descents, all the way to our final destination in Pienza.

Today’s ride takes you on a magnificent loop into the hilly terrain to the south of Pienza.

Leaving the hotel you’ll head west towards the town of Montalcino, home of the world-famous Brunello di Montalcino wine. We’ll stop for a coffee in the town center – and maybe a wee sip of the famous red stuff…! From Montalcino, get your climbing legs on as the terrain gets decidedly lumpy from here. The 8km (5 miles) climb to Poggio Rosa is a taste of what’s on the agenda for tomorrow. From Poggio Rosa enjoy the descent through Castiglione and into the flat Orcia valley, before the final sting in the tail with the climb back to your hotel in the hilltop town of Pienza.

The Queen Stage of the trip with the major climb to Monte Amiata. With an elevation of 1,738m (5,700ft), Amiata is the highest peak in Southern Tuscany – and just too tempting not to include in our itinerary!

Enjoy the initial descent from Pienza – but remember that you’ll have to climb back up this descent at the end of the ride! The route heads south through Poggio Rosa to Castel del Piano where the serious climbing starts. The summit, with it’s fantastic café and gelato bar, lies 15km (9 miles) up the road at an average of over 7%, putting Amiata up there with some of the big climbs in the Alps. Forza!

Unfortunately, your trip across Tuscany has come to an end.

Our shuttle will drop you off at Florence Airport.