Cycle San Gimignano to Siena

Cycle San Gimignano to Siena

Trip Highlights

  • 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 e-bike for your Tuscany cycle experience

Trip Summary

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. At night stay in characterful family run hotels where your hosts will introduce you to the delights of their local sites and trattorias.


This trip involves 3 days cycling usually along backroads and field paths with minimal car traffic (although some short distances will have heavier traffic) – the actual trail will depend on the type of bike you are riding which has a corresponding route. Hills are a common feature of the Tuscan landscape and this does require more effort when cycling – some hills are quite steep! The hybrid route is along backroads and a few off roads, whilst the mountain bike route follows trails and “Strade Bianche” (unsurfaced rural roads). The trip requires a good to excellent level of fitness with good uphill cycle legs to fully participate in this adventure. You need only carry your camera and water bottle. Your luggage is transported for you between hotels.


Make your own way to 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. 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.

Meals:  D

The scenery changes a lot today: from gentle hills cultivated with vineyards and olive groves, to extensive Mediterranean forest, into wide open fields cultivated with grain, sunflowers and medicinal herbs for animals. A characteristic is also the fine tufa stone soil which often presents an erosion phenomenon. Volterra is very interesting, an early departure is advisable to have more time to explore the town, especially in the summer time as the last part of the ride will not offer a lot of shade. Volterra is a former Etruscan town with a commanding position high on a rocky plateau. More recently it was featured in the second ‘Twilight’ movie, “New Moon”. Accommodation: Our first choice is in a welcoming and comfortable 3 star hotel, which is in fact a restored villa from the late 17th century. It is situated in a peaceful area near the medieval town wall. The hotel has a magnificent panoramic view of the area. All rooms are ensuite and the hotel also boasts an outdoor swimming pool.

Meals:  B

Two options are available to you again today. Option one passes through the small town of Colle di Val d’Elsa while option two crosses the natural reserve of Tatti, to the medieval town of Casole. Both rides visit the monastic settlement of Abbadia Isola. Overnight in the medieval walled village of Monteriggioni with its famous watchtowers. Accommodation: La Signoria 1212. Il Piccolo B&B in Monteriggioni offers accommodation in Monteriggioni. The rooms are equipped with a flat-screen TV the rooms come with a private bathroom. La Signoria Piccolo B&B features free WiFi throughout the property. You will find a shared lounge at the property. You may wish to upgrade to a 4 star inn, ask for details.

Meals:  B

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. 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 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. Accommodation: Comfortable town hotel in rooms with en suite facilities, telephone, and TV. The hotel is located walking distance from the train station or bus terminal.

Meals:  B

After breakfast make your own way to the train station for onward travel.

Meals:  B

What's Included

  • 4 continental breakfasts, 1 dinner
  • 3 nights accommodation in 3 star hotels and 1 B&B on a twin share basis
  • Luggage transfer (1 bag per person not weighing anymore than 20kg)
  • 5 day service hotline
  • Information kit including detailed maps and route notes

What's Not Included

  • Travel to and from San Gimignano and Siena
  • Mountain or Hybrid bike €80 or €150 E-Bike hire paid locally.
  • Meals not listed
  • Drinks
  • Items of a personal nature
  • Storage of luggage and parking
  • Transfers

Upcoming Travel Dates


Duration:5 Days
Starting Point:San Gimignano
Finishing Point:Siena
Activities:Self-Guided Cycling
Grade:moderate to challenging  Click for more information
Trip Code:TC5
Prices From:GBP£820 Per Person
single supplement:GBP£240  Click for more information
solo traveller:GBP£360  Click for more information