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Siena 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 the tranquil Arezzo.

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.

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 Start Stay Core route Options En Route
→ km ↑ m longer shorter
1 - Siena - - - -  
2 Siena Montalcino 51 1020 The Siena hills, the Etruscan lands of Murlo, the town of Buonconvento
3 Montalcino Montepulciano 47.3 635 The small hilltop villages of the Val d’Orcia, Montepulciano
4 Montepulciano Montepulciano 63.8 869 The gravel road to La Foce, the hot springs of Bagno Vignoni, the Val d’Orcia UNESCO site, Pienza
5 Montepulciano Cortona 40 544   Chiana Valley, Vino Nobile Wine production Territories
6 Cortona Cortona 68.7 725   The Upper Tiber Valley in Umbria, views of Trasimeno, Citta di Castello
7 Cortona Arezzo 35.4 460     Anghiari, the St Francis way, the Arezzo valley

Tour Costs

Costs in Euros
Basic cost per person sharing 775*
Single accommodation supplement (if applicable) 295
Optional Costs
Bicycle rental Hybrid 145
Road 185

Carbon Road Bike 275

E-Bike POA
luggage transfers Total for one or two people 305
Each additional person 25

* Prices for solo travellers are on request

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

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