Siena & Tuscany

Independent Tour.8 Days / 7 Nights Approx 300km

The Tuscan countryside is a patchwork of vineyards and olive groves, ancient forests, and fields of wheat and barley. There are long views over roling hills, many crowned with medieval cities and villages - San Gimignano, Pienza Monterrigioni and Colle Val D’Elsa. A wealth of art and architecture awaits.

Your journey takes you through the Val d’Arno, Val d’Orcia, the old Roman Road - the Via Francigena, and Chianti.

You will be cycling through some of Italy’s best wine-producing areas with many opportunities to taste at the friendly ‘enoticas’ - Brunello from Montalcino, Vino Nobile from Montepulciano and Chianti Classico from Chianti of course! In the evenings enjoy typical Tuscan fare of game, steaks, wild mushrooms, beans, truffles and home-made pasta.

Your Journey

Day 1 Arrive Siena:

Visit the fabulous Duomo with it’s marble floors and the Piazza del Campo where the centuries-old Palio horse races are held annually.

Day 2 Siena – Castelnuovo Berardenga – Asciano (49 km):

Cycle through the typical southern Siena landscape known as the 'crete senesi'. You reach the southern boundary of the Chianti region at Castelnuovo.

Day 3 Asciano – Monte Oliveto – San Giovanni d’Asso - Pienza (52 km):

Cycle to the great abbey of Monte Oliveto Maggiore then on to the wonderfully preserved tiny Renaissance ‘city’ of Pienza for overnight.

Day 4 Pienza – San Quirico – Montalcino - Buonconvento - Murlo (56 km):

Cycle along the Via Panoramique to the medieval walled town of San Quirico then up a steep climb to Montalcino, heart of the Brunello wine district. Enjoy the roll down to tiny Murlo for overnight.

Day 5 Murlo – Radi – Sovicille – Monteriggioni - Colle Val d’Elsa (64 km):

Cycle the outskirts of Siena past the 13C walled village of Monteriggioni. Continue to Colle Val d’Elsa and enjoy a stroll in the Old Town.

Day 6 Colle Val d’Elsa – Casole d’Elsa – Ulignano – Volterra (47 km):

Cross a valley and two ridges to Volterra. Explore its medieval streets, Etruscan walls, gateways and tombs.

Day 7 Volterra – Certaldo (40 km):

Cycle through an almost unchanged medieval landscape to San Gimignano, a walled medieval town whose ‘towers’ are a landmark. Continue to the hill town of Certaldo. Transfer by train to Siena (not included).

Day 8 Siena:

Arrangements end in Siena after breakfast.


Cycling on country roads, strada bianca (gravel roads) and short stretches of main roads near towns. Tuscany is hilly and the route has been planned to avoid as many as possible. Grade is moderate with some steep climbs.

Contact Us

  • 306 Lake Road, Takapuna
    Auckland 0622, New Zealand
  • P: (0064) 09 486 7473
    F: (0064) 09 484 0091

Contact Form

Connect with us

About us

Cycling Europe Offers Cycling Holidays in Europe and around the world.

  • Our experienced team can advise and coordinate your travel arrangements to your personal requirements.