Iron Donkey Bicycle Touring | Bike Tours in Ireland England Wales Scotland Italy Spain
Iron Donkey Bicycle Touring : bike tours, cycle vacations and biking holidays in Ireland, England, Wales, Scotland, Italy and Spain.

Tuscany Extended Self-Guided Tour (12 Nights)

Tour code: TUSSG12

Tour Overview

This is a comprehensive tour that combines the routes through western Tuscany with the routes through the Siena region. The itinerary is designed to show off the very best that Tuscany has to offer!

The first route leads from Siena through gently rolling terrain to the walled town of Monteriggioni en route to Colle di Val d’Elsa. From here you continue west to the medieval Manhatten that is San Gimignano. Continuing west you tackle the ascent to Volterra. The ride south from Volterra to Marina di Bibbona takes you through the Val di Cecina and the Metalliferous Hills. A loop ride from Marina di Bibbona explores the coastline to the north. The next stage takes you inland to the beautiful town of Massa Marittima. From here you pedal east to Monticiano and Montalcino. Two nights are spent in Montepulciano before dropping down to cross the Val d’Orcia and then turning north to Monte San Savino. Cortona (of Under The Tuscan Sun fame) is the penultimate destination before you complete the adventure with a climb over the hills to Sansepolcro in the Upper Tiber Valley.

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

Ten highlights

  • Sodoma’s frescoes in the Abbazia di Monte Oliveto Maggiore
  • The Renaissance town of Pienza
  • Tthe 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
  • San Gimignano – the medieval Manhatten
  • The alabaster workshops of Volterra
  • The Tuscan Coast around Marina di Bibbona
  • San Galgano Abbey
  • The Montagnola Senese


  • Bagno Vignoni
  • Portoferraio, Elba
  • Strade Biancha
  • Val D'Orcia
  • White Road


  • Spend a night or two in Florence before or after your bike tour.
  • Spend an additional night or two on the island of Elba.

Outline Itinerary

Day Itinerary Start Finish Route options
En Route
1 arrive at SIENA        
2 route A Siena San Gimignano    
Colle di Val d'Elsa; Monteriggioni; Chianti
3 route B San Gimignano Marina di Bibbona    
Volterra; Montecatini Val di Cecina; Metalliferous Hills
4 route C Marina di Bibbona Marina di Bibbona    
Montescudaio; Guardistallo; Monteverdi Marittimo; Castagneto Carducci
5 route D Marina di Bibbona Massa Marittima    
S.Vincenzo; Venturina; Suvereto; Montioni
6 route E Massa Marittima Monticiano    
Lago Accesa; Ghirlanda; Montieri; Chiusdino
7 route G Monticiano Montalcino    
river Merse valley; St Antimo
8 route I Montalcino Montepulciano  
S. Quirico d'Orcia; Pienza;Montisi; Catelmuzio; Radicofani; Sarteano
9 route J Montepulciano Montepulciano    
Monticchiello; Pienza; La Foce; Bagno Vignoni; Bagno Vignoni; Petroio
10 route K Montepulciano Monte San Savino    
Terme di Rapolano; Val di Chiana
11 route N Monte San Savino Cortona    
Val di Chiana; Foiano; Pozzuolo; Lake Trasimeno
12 route P Cortona Sansepolcro    
Alto Tevere Umbro; Città di Castello; Monte Santa Maria Tiberina
13 depart from SANSEPOLCRO        

Tour Costs

Costs in Euros
basic cost per person sharing
single accommodation supplement (if applicable)
Optional Costs
bicycle rental
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.

Make an Availability Enquiry for this tour »

« Back to previous page