Florence to Pisa

Self Guided 8 Days / 7 Nights 315 kms

Discover the highlights of the Tuscan countryside on this route between two important art cities. Start in Florence, the cradle of Renaissance and cycle in the heart of Tuscany, the famous Chianti and one of Italy’s best wine-producing areas. Siena, one of the best preserved medieval cities in Europe, waits 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 like San Gimignano, Colle Val d’Elsa and Volterra, just waiting to be discovered. Along the way enjoy 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’. Truly a tour to delight the senses!

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 but expect some steep climbs.  Hilly, rolling terrain with some climbs and descents (last stage mostly in descent). Cycling on asphalt roads and a few gravel country roads.


Breakfast daily.

Trip Notes / Dates / Prices 2019

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    Auckland 0622, New Zealand
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Cycling Europe Offers Cycling Holidays in Europe and around the world.

  • Our experts Jill, Therese, Adrienne, Lisa and Janne have over 100 years combined experience working in the travel industry.
  • Our team can advise and coordinate your travel arrangements to your personal requirements.