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Western Tuscany Self-Guided Tour (7 Nights)

Tour code: TUSSG7B

Tour Overview

This itinerary explores the lesser known, but no less beautiful areas of Tuscany to the west of the renowned Siena region.

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 ride east, visiting the ruins of San Galgano Abbey en route to Monticiano. The last leg completes the circuit by turning north across the Montegnola Senese back to Siena.

See the Regional Details page for further information on the scenery and attractions.

Ten highlights

  • Siena
  • Monteriggioni
  • San Gimignano – the medieval Manhatten
  • The alabaster workshops of Volterra
  • The Cecina Valley
  • The Tuscan Coast along the Maremma
  • The Tuscan Coast
  • Massa Marittima
  • San Galgano Abbey
  • The Montagnola Senese


  • Elba
  • Ice Cream
  • On The Road
  • Riding Into Town
  • Volterra


  • Spend a night or two in Florence before or after your bike tour.
  • Ride from Florence to Siena through Chianti stopping in the town of Greve in Chainti en route.
  • You can extend your trip by a couple of nights to visit the Island of Elba.

Outline Itinerary

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

Tour Costs

Costs in Euros
Basic cost per person sharing 755*
Single accommodation supplement (if applicable) 265
Optional Costs
Bicycle rental Hybrid 145
Road 185
Carbon road 285

E-Bike POA
luggage transfers Total for one or two people 490
Each additional person 20

* Prices for solo travellers are on request

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

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