After breakfast you leave Siena and cycle surrounded by a beautiful scenery of the hills of the Chianti Senese and le Crete with unforgettable panoramas of the Chianti vineyards and woodland. Worthwhile to visit is the castle of Brolio, surrounded by vineyards, which has Lombard origins. The tour of today finishes at Asciano. It has a nice medieval centre with a famous museum: the Museo Archeologico of Palazzo Corboli is classified by the Daily Telegraph as one of the fifteen Italy’s best small museums.

Distance 49 km / 30,4 miles –differences in altitude 830 m– 13km of dirt roads

Today you enter the Val d’Orcia with wide open skies, rolling hills lined with cypresses and meandering roads disappearing into the horizon. You pass the abbey of Monte Oliveto with its chiostro (cloister) decorated by Luca Signorelli and il Sodoma, the church renovated in Baroque style and the beautiful library. You can plan to make a stop in the medieval village of San Giovanni d’Asso, where you could visit the truffle museum. Another stop worth while is at the ex- monastery of S.Anna a Camprena, where other frescoes of Il Sodoma can be admired. Pedalling between fields with nice views you arrive at Pienza, a pearl of the renaissance.

Distance 52 km / 32 miles –differences in altitude 800 m– 12km dirt roads

A scenery with soft rolling hills, never ending grain fields, vineyards, olive groves, hay meadows and pastures for livestock will accompany you all day. Very interesting is the historical centre of S.Quirico d’Orcia with its 13th century hospital of S.Maria della Scala. This hospital offered shelter to pilgrims and travellers passing along the Via Francigena. The other two charming towns you will pass today are Montalcino, where you can enjoy a good glass of Brunello di Montalcino, and the medieval village of Murlo.

Distance 56 km / 34,7 miles –differences in altitude 750m– 15km dirt roads

Today’s ride is following for a big part the Via Francigena, a pilgrimage way which in 79 stages connects Canterbury with Rome, crossing France and Switzerland before entering in Italy. Already from afar you will see the impressing town walls of Monteriggioni. These walls are covering a length of 570m alternated by two town gates and 14 towers. Here you could make a lunch stop to taste some of the local specialities like Panzanella, la Finocchiona and baccelli, funghi in gratella (mushrooms) and l’agnello arrosto con piselli e patate alla ghiotta (lamb meat with peas), combined with a good Chianti. Your overnight stay will be in Colle Val d’Elsa.

Distance 64 km / 39,7 miles –differences in altitude 680m–mixture of dirt roads and asphalted roads

Some uphill and downhill cycling will bring you to Volterra, an Etruscan town famous for its alabaster production. From Etruscan times remain the two town gates Porta all’Arco and Porta Diana and numerous tombs. In the centre you can visit 4 museums: the Museo Etrusco, Pinacoteca Civica, Museo d'Arte Sacra and l'Ecomuseo dell'Alabastro.

Distance 47 km / 29 miles – differences in altitude 1110m– mixture of dirt roads and asphalted roads

This last day you will cycle to San Gimignano, famous all over the world for the skyline of its medieval towers. This town dominating the Valle d’Elsa was very important during medieval times because of its position along the Via Francigena. In the surrounding countryside we find the cultivation of saffron. By bike you will reach Certaldo and from here you take the train to Siena, end destination of this tour.

Distance 47 km / 29 miles – differences in altitude 600m– mixture of dirt roads and asphalted roads