Cycle San Gimignano to Siena
All content by World Expeditions
A shorter version of our popular Tuscany Cycle Explorer
Experience the magic of Tuscany's countryside on an enlightening cycle through the enchanting towns and landscapes that characterise the region. Every day brings with it a diversity of sites including ancient monasteries, rolling vineyards and old olive groves, castles, villas and medieval centres ripe for exploration. Flexibility is a key component with the option to choose a tarmac road or off road mountain bike route according to your level of cycle experience. At night stay in characterful family run hotels where your hosts will introduce you to the delights of their local sites and trattorias.
- Cycling through the beautiful Tuscan countryside
- Experiencing fabulous towns such as Volterra, San Gimignano and Siena
- Enjoying the fantastic cuisine of the region
- Choose between a mountain bike, hybrid or racing bike for your Tuscany cycle experience
Day 1 Arrive San Gimignano
The trip begins at the first hotel in San Gimignano, known as the town of the beautiful towers which have dominated the hills south of the Elsa Valley since Etruscan times. There is much to explore in this small town, in particular the narrow streets and squares of the medieval quarter. Overnight in San Gimignano. Dinner is included this evening (except on Tuesdays when the restaurant is closed – in this case your evening meal will be included in Monteriggioni on Day 4). Your bike will be personally delivered either this afternoon or tomorrow morning. Accommodation: Our first choice is a 3-star hotel set in the pulsating heart of the town of towers, little changed for 600 years. The view from the rooms is mostly outstanding.
Day 2 Cycle to Volterra (37/48/83km)
A spectacular ride westwards over the hills to Volterra and for a more challenging day visit the Monastery of San Vivaldo. Racing bikes will also discover the lovely towns of Orciatico and Montecatini. Overnight in Volterra, a former Etruscan town with a commanding position high on a rocky plateau. More recently it was featured in the second ‘Twilight’ vampire movie/book, “New Moon”. Accommodation*: Our first choice is in a welcoming and comfortable 3 star hotel, which is in fact a villa from the late 17th century that has been restored. It is situated in a peaceful area near the medieval town wall. The hotel has a magnificent panoramic view of the area. All rooms have their own shower and toilet. The hotel also boasts an outdoor swimming pool.
Day 3 To Monteriggioni (41/59/82km)
Two options are available to you again today. Option 1 passes through the small town of Colle di Val d’Elsa while option 2 crosses the natural reserve of Tatti, to the medieval town of Casole. Both rides visit the monastic settlement of Abbadia Isola. The racing bike riders will also visit Montecastelli and Monteguidi. Overnight in the medieval walled village of Monteriggioni with its famous watchtowers. Accommodation: A small guest house within the medieval walled village of Monteriggioni; once the day-visitors have gone it is a haven of peace; the rooms (limited in number) are simply furnished, but all have private facilities and offer splendid views on the town and the surrounding country side.
Day 4 Cycle to Siena (25/35/65km)
The last day of cycling takes you to the interesting “Palio” town of Siena. En route cycle via the cantines and test the wines of Dievole on a longer route through the Chianti hills. The proprietor is always ready to take you on a memorable tour, before continuing to Siena. The longer route takes you to Brolio, whilst the racing bike route is a circuit through the Crete Senesi hills, with the highlight of a visit to the monastery of Monte Oliveto. There is also a more direct route for those interested in spending more time in Siena. After settling into the hotel you will find all the famous places of this city within walking distance, with the Palazza il Campo being the famous centre of this medieval city. There are many museums, churches, and the huge Pisa Romanesque and Gothic cathedral. You can easily get lost in the warren of streets, all arranged into areas called "Contrada," as they have done for hundreds of years and from where the Sienese population gain their group loyalties and rivalries. Overnight Siena. Accommodation: a comfortable town hotel in rooms with en suite facilities, telephone, and colour TV. The Hotel is located at a walking distance from the train station or bus terminal.
Day 5 Trip concludes
Trip concludes after breakfast. *Note: The accommodation indicated above is subject to availability. Where the first choice hotel is not available we will book you in alternative comparable accommodation.
- 4 breakfasts, 1 dinner – continental breakfasts are served and usually consist of breads, jams, coffee, tea and juices.
- 4 nights accommodation in 3 star hotels and B&B’s on a twinshare basis – chosen for their local character.
- Mountain or hybrid bike. Racing bike available for small supplement.
- Luggage transfer
- 7 day service hotline
- Information kit including detailed maps and route notes
Group Size Min
Group Size Max
Accommodation is on a bed and breakfast basis in 3 star hotels and guesthouses or agritourismos (farmhouses) always with en-suite facilities. One dinner is included (either in San Gimignano or Monteriggioni); the other evening meals can readily be obtained locally without pre-booking, but are not included in the trip price. Picnic lunches are not included in the price, but materials for picnics can be purchased in each of the towns and villages where you stay. Our standard accommodation is subject to variation: This is a very popular route and we sometimes have to use alternatives to the hotels described in the itinerary above. These are however of a comparable standard. From the moment you book to your arrival we also try to upgrade your booking into our first choice Inn – you will get a note about this on your arrival if applicable. Extra Nights – It is possible to include extra nights in Castellina in Chianti, Volterra, S.Gimignano, Monteriggioni and Siena. Extra nights in the middle of the trip need to be requested at the time of booking.
Wet weather gear, sunscreen, bike helmet and sun hat.