8 days - Self-guided cycling

1° day: Siena Arrival in Siena. You can also stay in Pisa and take a train (90 min - dep. at 08.30 a.m.) to Siena the following day.

2° day: Siena - Radda in Chianti (40 km) From Siena you start to head north towards the beautiful village of Radda in Chianti. This town is situated on a hill covered with woods and extensive vineyards forming the watershed between the Pesa and Arbia valleys. Formerly belonging to the Guidi family, it came under Florentine control in 1203. After being fortified in 1400 it was, from 1415 onwards, head of the League of Chianti, and it preserves the remains of its ancient walls.

3° day: Radda in Chianti - Greve (30 km) Today the route brings you to Greve over the rounded Tuscan hills with beautiful views.

4° day: Greve - Florence (38 km) Florence, capital of the region of Tuscany spreads on the banks of the Arno, between the Adriatic and the Tyrrhenian seas, almost in the middle of the Italian peninsula. Two of the many artists associated with Florence are Leonardo da Vinci and Michelangelo Buonarroti.

5° day: Florence - Tavernelle (47 km) The village of Tavernelle Val di Pesa has Roman origins; it is named after the ancient taverns offering accommodation and refreshment located along the road which linked Florence to Siena and thence to Rome. The territory of Tavernelle, like the entire Chianti district, has a particularly rich heritage of rural building: churches, oratories, chapels, villas and farms.

6° day: Tavernelle - Colle Val d'Elsa (45 km) From Tavernelle it is on to Colle di Val d'Elsa which lies in the heart of Tuscany, in a strategically favourable position near the towns of Siena and Florence on the via Francigena that connects Rome with the North. On the way we pass Certaldo, whose upper part has remained as it was in the Middle Ages. Here you can admire the Palazzo Pretorio (12th cent.) and the house of Giovanni Boccaccio, the author of the Decameron. Further on we come across San Gimignano, which rises on a hill dominating the Elsa Valley with its towers. Once the seat of a small Etruscan village of the Hellenistic period (200-300 BC) it began its life as a town in the 10th century and increased in wealth and developed greatly during the Middle Ages.

7° day: Colle Val d'Elsa - Siena (37 km) From Colle Val d'Elsa you will cycle to the beautiful town of Siena which, is not only one of the most fascinating towns in Tuscany but is also in a particularly beautiful position, with lovely environs. It preserves its medieval character to a remarkable degree, and has been largely unspoilt by new buildings. Its beautiful Gothic buildings include the Cathedral and Piazza del Campo on the characteristic Piazza del Campo, as well as numerous churches.

8° day: Siena Departure.

Tour Level:
Heavy, with sloping landscapes dot-ted with steeper inclines, but not overwhelmingly so. Average daily distance is about 40 kilometers. Though the daily routes are not too long, they can be strenous, so we do recommend being in reasonably good physical condition for this tour.