Florence to Siena to Pisa

Self Guided 8 Days / 7 Nights 315 kms

This bike tour reads like a Tuscan dream with names like Volterra, San Gimignano, Greve in Chianti, Pisa, Siena and Florence all popping up along the route. It starts in the famous ‘art city’ of Florence, the cradle of Renaissance from where you cycle the splendid Chianti countryside, one of Italy’s great wine-producing areas. From here Siena, one of the best preserved medieval cities in Europe, awaits with its’ wealth of art and architecture. The Tuscan countryside is a patchwork of vineyards and olive groves, ancient forests, fields of wheat and barley. There are wonderful views over rolling hills, many crowned with medieval towns and villages.
End the day dining on typical Tuscan fare of game, steaks, wild mushrooms, beans, truffles and homemade pasta plus opportunities to taste the rich reds and crisp white wines at the friendly ‘enoticas’.

Your Journey

Day 1

Arrive Florence.  Allow time to visit the famous Duomo, Uffizi Gallery, Academia to see the statue of Michelangelo’s David, and the markets.

Day 2: Florence – Greve in Chianti  (44 km)

Cycle to Impruneta, the town of terracotta art then on to Mercatale, a small town surrounded by the Chianti hill.  You will be able to taste wine and other products in the wine cellar of a charming castle.

Day 3: Greve in Chianti – Radda in Chianti  (31 km)

Today you will discover one of the best known areas of Tuscany: "strada del vino” (the road of wines).  The Classic Chianti, situated between Florence and Siena, appears like a hilly landscape, varied and colourful. Here the famous wine have been produced since Etruscan times.

Day 4 Radda in Chianti - Siena 41 km

From Radda in Chianti, cycle to Siena via the castles of Meleto (now transformed into a magnificent Tuscan villa)  and Brolio where you can have a wine tasting in the Ricasoli wine cellar.  In Siena there are some of the most remarkable monuments in Italy: Piazza del Campo and Public Palace; Buonsignori Palace with the National Pinacoteca (where you can admire pictures of Duccio, Lorenzetti, S. Martini etc); the Cathedral built from the 12th century with a façade of white and dark-green marble; the Piccolomini Library; the Baptistry and the Museum of Metropolitan Work.

Day 5 Siena – Colle Val d’Elsa (27 km)

Cycle over rolling hills, along a section of the ancient Via Francigena (Path To Rome) alongside Mount Maggio.  In the distance you can see Monteriggioni’s castle before you arrive at Abbadia a Isola, a resting place along the Via Francigena and notable for its church entrance that resembles that of the Church of the Holy Sepulchre in Jerusalem. Continue to Colle Val d' Elsa, an ancient Etruscan town known for crystal and glass making.

Day 6 Colle Val d’Elsa - Volterra (46 km)

From Colle Val d’Elsa cycle to walled, hilltop San Gimignano, a splendid example of a well-preserved Medieval city that is distinctive due to its’ four landmark towers.  The Via Francigena passes right through the town.  Late afternoon arrive in Volterra, a city with over 3,000 years of history dating back to Etruscan times.

Day 7 Volterra - Pisa (54 km):

Depart Volterra to Ghizzano, a village surrounded by vineyards. Continue along a beautiful route to reach Calcinaia on the Arno River which you follow to the confluence of the Era and Arno Rivers at Pontedera from where you take a short train trip to Pisa, the city of the Leaning Tower.

Day 8:

Tour ends.  Allow time to visit the Cathedral, the Baptistery and the Leaning Tower.


Moderate to energetic due to the hilly terrain of Tuscany. E bikes and a good drop of Chianti at the end of the day will help!


Breakfast daily.

Trip Notes / Dates / Prices 2020

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    Auckland 0622, New Zealand
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