Tuscany Cycle Explorer

Tuscany Cycle Explorer

Trip Highlights

  • Cycling through the beautiful Tuscan countryside
  • Experiencing fabulous towns such as Volterra, San Gimignano and Siena
  • Exploring the Chianti region at handle bar level
  • Enjoying the fantastic cuisine of the region
  • Choosing between a mountain bike or hybrid 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. 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.


Moderate. A high standard of fitness is not necessary but clients should be able to cycle for up to 45 km/28miles per day across undulating hilly terrain in rain or sun. Most days can readily be shortened.


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: For two nights, 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 first day of cycling takes you on a circuitous route through the countryside around San Gimignano, through vineyards and traversing gentle hills. The ride takes you to Certaldo through Vernaccia, San Gimignano’s white wine vineyards. The route will depend on the bike you have chosen. Alternatively you are free to relax around San Gimignano where you again spend the night.

Meals:  B

A spectacular ride westwards over the hills to Volterra and for a more challenging day visit the Monastery of San Vivaldo. Volterra is 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: Comfortable 3 star hotel, 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. 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

Today you will be cycling into the Chianti Hills and you will have the opportunity to sample several Chianti wines. The high point of the ride is Fonterutoli and the incredible open views. Accommodation: Two nights in a B&B with loads of charm. The rooms are simply appointed but very comfortable in typical Tuscan style.

Meals:  B

A circular ride today throughout the Chianti Hills visiting some of the most beautiful villas, castles and rural churches.

Meals:  B

The last day of cycling takes you to the interesting “Palio” town of Siena. En route visit the cantines and test the wines of Dievole. The longer route takes you to Brolio. After settling in to 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 Pisan 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 where the Sienese population gain their group loyalties and rivalries. Accommodation: In the lively and sophisticated city of Siena we stay at a small, comfortable 3 star town hotel, all rooms ensuite.

Meals:  B

Trip concludes after breakfast.

Meals:  B

What's Included

  • 7 breakfasts, 1 dinner
  • 4 nights in 3 star hotels, 2 nights in guesthouse and 1 night in a B&B on a twin share basis with ensuite facilities
  • Information pack including route notes & maps
  • Luggage transfer (1 bag per person not weighing anymore than 20kg)
  • Emergency hotline

What's Not Included

  • 6 dinners, all lunches & beverages
  • Mountain or Hybrid bike €100 or E-bike €180 hire paid locally
  • Travel to and from San Gimignano and Siena
  • Entrance fees
  • Travel insurance
  • Travel to the start and from the end point of the trip
  • Personal expenses such as laundry and phone calls
  • Unscheduled transfers required during the trip

Upcoming Travel Dates


This was a fantastic holiday which all four of our group enjoyed to the full. The routes were through the most stunning countryside, the accommodation was superb, the overnight stops were in fascinating and charming villages and towns. Quiet cycling routes.

R. Mackichan, Worcester, UK, 25 Oct 2016

This was a great trip for our group of six. The Tuscany landscape is truly beautiful; our accommodations were comfortable and the historical towns we stayed in were worth exploring. The cycling is certainly medium to hard; although most roads were quiet and vehicle traffic was mostly respectful of cyclists.

D. Parry, Sylvan Lake, Alberta, Canada, 25 May 2017


Duration:8 Days
Starting Point:San Gimignano
Finishing Point:Siena
Activities:Self-Guided Cycling
Grade:moderate  Click for more information
Trip Code:TCA
Prices From:GBP£1030 Per Person
Single Supplement:GBP£400  Click for more information
Solo Traveller:GBP£600  Click for more information