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Siena Self-Guided Tour Self-Guided Tour (7 Nights)

Tour code: TUSSG7A

Tour Overview

Siena is without doubt the showpiece province of Tuscany, and this itinerary shows it off in all its glory. The incomparable impressionist-style landscapes of lush vine and poppy bedecked hills and valleys just beg to be explored and enjoyed from the saddle of a bicycle.

Starting at the fabulous city of Siena, the tour takes you first to the green pasturelands of Le Crete where tiny roads wind through the fields and along hill crests to connect ancient farmhouses and tiny medieval villages. This area is a scenic delight of bare ridges, solitary cypresses and medieval farmhouses, and it abounds with ancient Roman and Etruscan archaeological sites. South from Le Crete lies the Val d’Orcia where the landscape is one of nature’s inspired works of art. Possibly no other region conjures up such classical images of Tuscany. ... the hamlets and hilltowns, terracotta rooftops, swaying cypress and golden valleys, vineyards and olive groves all contribute to the overall picture. Besides the beauty of the landscape, you will explore the fascinating and beautiful towns of Pienza, Montepulciano and Montalcino. Dropping down from Montepulciano you pedal through the the sunflower, tobacco and corn fields of the Val di Chiana to Monte San Savino before climbing to the spectacular city of Cortona. The final leg of the itinerary is a beautiful ride across the hills to Sansepolcro on the Umbrian border.

This tour is Tuscany cycling at its very best. Each core route is designed to allow time to enjoy the scenery, to explore the en route attractions and to have a leisurely lunch. The route extensions are for the more ambitious riders who want to challenge themselves. It is important to bear in mind that Tucscany is not flat – even on the core routes the terrain is largely rolling. Some of the riding on both core routes and extensions is on the strade bianche - the white dirt roads that are so characteristic of Tuscan landscapes.

See the Regional Details page for further information on the scenery and attractions.
The itinerary follows routes H, I, J, K, N and P
The tour is rated B – click here for tour rating description.

Ten highlights

  • The views from Siena’s Torre del Mangia
  • Siena Cathedral
  • Sodoma’s frescoes in the Abbazia di Monte Oliveto Maggiore
  • The Etruscan museum in Murlo
  • The Castle of Gargonza
  • The Renaissance town of Pienza
  • The hot springs in Bagno Vignoni
  • Sampling a glass of Brunello wine in Montalcino’s Fortezza
  • The vista across the Val d’Orcia from Cortona’s heights


  • Admiring The Scenery
  • Cortona
  • Montepulciano
  • Road To Pienza
  • Visitor Attractions


  • Spend a night or two in Florence before or after your bike tour.
  • Ride from Florence to Siena through the Chianti region, stopping in the town of Greve in Chianti en route.
  • Link this itinerary seamlessly to the Umbria self-guided itinerary to produce a 13 night trip through Tuscany and Umbria.

Outline Itinerary

Day Itinerary Start Finish Route options
En Route
1 arrive at SIENA          
2 route H Siena Montalcino    
Ville di Corsano; Buonconvento; Monte Oliveto Abbey; St Antimo
3 route I Montalcino Montepulciano  
S. Quirico d'Orcia; Pienza;Montisi; Catelmuzio; Radicofani; Sarteano
4 route J Montepulciano Montepulciano    
Monticchiello; Pienza; La Foce; Bagno Vignoni; Petroio
5 route K Montepulciano Monte San Savino    
Terme di Rapolano; Val di Chiana
6 route N Monte San Savino Cortona    
Val di Chiana; Foiano; Pozzuolo; Lake Trasimeno
7 route P Cortona Sansepolcro    
Alto Tevere Umbro; Città di Castello; Monte Santa Maria Tiberina
8 depart from SANSEPOLCRO          

Tour Costs

Costs in Euros
basic cost per person sharing
single accommodation supplement (if applicable)
Optional Costs
bicycle rental (hybrid)
bicycle rental (road)
bicycle rental (carbon road)
luggage transfers
shared charge for group
additional charge per rider

* There is an additional charge of 100 Euros for someone who is travelling on their own.

Click here for more details on what's included in the costs above.

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