Cycling South of Siena

Cycling South of Siena

Trip Highlights

  • Biking through vineyards, forests, fortified villages and hilltowns of Southern Tuscany
  • Windnig your way through a medieval painting
  • Wine tasting and Roman Baths

Trip Summary

This is a more challenging cycling tour than our ‘Treasures of Tuscany’ ride and takes you to see the quieter side of Tuscany, to the south of Siena. Starting from this beautiful bustling city, almost suspended in medieval animation, you pedal off into a photogenic Tuscan landscape of gentle hills (known as the Cretes), tipped by lonely umbrella pines or oaks. While the famous Tuscan cypresses line the trails leading to the distant farmhouses, and the white roads that you will often be cycling down. On the way down through the Chianti districts and then into the beautiful Brunello wine country, you will pass by one of the most attractive convents of Tuscany at Monte Oliveto Maggiore. This is a typical red brick monastery where friars of the Benedictine Order still worship. From Buonconvento the route rises uphill through the vineyards of San Giovese grapes as far as the walls of Montalcino offering breathtaking views and of course Brunello wine. Another peaceful ride takes you to the St.Antimo Abbey. A unique structure in pure Romanesque form where the warming murmur of prayers and songs, spoken by French Gregorian friar’s echoes through the cloisters. If cycling has made you work up a sweat then it will now be time for you to discover the hot springs at Bagno Vignoni, used in renaissance times by Lorenzo de Medici and by the Popes. There is a huge pool of sulphurous water in which to unwind. With exceptional views you will then approach the huge medieval bastion of Montepulciano, a stiff climb in places, but you should promise yourself that when you reach this, one of the highest towns in Tuscany - with views extending over Umbria; you will buy a bottle of the famous Vino Nobile to celebrate your arrival where our tour ends.


Moderate to Challenging. By the nature of the Tuscan landscape, this tour involves hilly riding. There is a maximum altitude variation of 1870 metres overall on one day’s ride. Most of the days are on a mix of terrains / surfaces including ‘Strada Bianchi,’ white gravel roads, and farm tracks. It is not technical mountain biking, although steep sections with loose surfaces will be encountered. All days have easier or shorter options, often involving a more direct tarmac route. Note however that road routes into the hill towns can be busy at times due to tourist and local traffic and of course narrow roads. On the whole though Italian drivers are used to cyclists. Fitness: Clients should have a reasonable level of fitness and should be able to cycle up to around 50kms in hot sun on dusty or stony tracks.


Make your own way to Siena. Travel by train from Pisa or Florence via Empoli. From the train station the hotel is a 10 minute walk or short taxi ride. You can travel by bus from Rome or Florence with the hotel a 5 minute walk from the bus station. After settling into the hotel you will find all the famous places of the city within walking distance, with the Duomo, the huge Pisan Romanesque and Gothic cathedral, the Palazzo Salimbeni, (the ancient head-quarters of the Monte dei Paschi di Siena, the oldest bank of the world, founded in 1472 and still today one of the biggest banks in Italy) and the Piazza del Campo, the shell like square, centre of the medieval city, where twice per year they hold the “Palio” horse race. You can easily get lost in the warren of streets of Siena! Accommodation: In the lively and sophisticated city of Siena we stay in a small comfortable 3 star town hotel. All rooms are ensuite.

Meals:  Nil

Your first cycling day is through the Chianti Hills. From here you cross the fascinating area of hills called the Crete Senesi reaching the Monastery of Monte Oliveto Maggiore, built in the 14th century by the Olivetan monks. Surrounded by a forest of cypresses, this place is world famous for the frescoes in the courtyard painted by the 15th century painters Signorelli and Sodoma. The library and the church of the convent are also architectural masterpieces. You then continue on until you reach the small town of Buonconvento, where the Emperor Henry VII died in 1313. Quite a tough day. Accommodation: Overnight in a renovated 3 star hotel, which is located in the centre of the town.

Meals:  B

Today you will pass some wonderful villas and castles. You will then cross the Ombrone River and come into the wine producing area of Brunello de Montalcino. Overnight in Montalcino. Distance: 38km. There are also options for a shorter 14km tarmac ride and a 25 km mixed surface ride. Accommodation: Stay in a 3 star hotel where you will have magnificent views. The hotel has a small swimming pool to cool off in the warmer months. This is a wonderful town with lots to do and see and we would recommend an extra night if you wish to extend your holiday.

Meals:  B

A free day in Montalcino either relaxing by the pool or alternatively a ride to visit the village of Sant'Angelo in Colle, have lunch at one of the finest farmhouses in Tuscany, the Banfi property. On your way back there are castles and villas to be explored. 41 km mixed surface ride of medium difficult.

Meals:  B

Today's cycle will take you to the romantic abbey of Sant Antimo, one of the most beautiful in all of Tuscany and now lived in by the French Gregorian friars. Their prayers and songs give the ambience a special mystic atmosphere. From here make a visit to the medieval town of Castelnuovo dell’Abate, with great views across to Monte Amiata, a former volcano, which is still important for its thermal water. From here you continue and cross the Canyon of the Orcia River. On your side of the Canyon is the castle of Ripa d’Orcia, and on the opposite side there is the castle of Rocca d’Orcia. You then reach Bagno Vignoni, which was built in the 13th century to permit Lorenzo de Medici and the popes to relax in healthy thermal water. In this small village, instead of the usual central square, there is a large pool! Especially on cooler days the effect of the rising steam is incredible. Medium / difficult route mainly on gravel roads. Distance: 34km. Easier tarmac road option 33km. Accommodation: Il Loggiato BB dates back to the 13th century, it has 6 rooms so has that lovely personal feel to it.

Meals:  B

Cycling through open countryside that will lead you to a Renaissance jewel, Pienza. Cycle through the pleasant village of Monticchiello, a surprising small village located on the top of a hill with a marvelous surrounding view before you reach your last amazing bastion, the medieval town of Montepulciano. This has one of the most impressive renaissance buildings in Italy: the church of San Biagio. Distance: 29km, mainly on unpaved roads. Easier 27.5 km option available. Accommodation: Overnight in a family run 3 star hotel, there are also several properties that we use in the centre.

Meals:  B

Arrangements end after breakfast

Meals:  B

What's Included

  • 6 breakfasts
  • 5 nights accommodation in 3 star hotels on a twin share basis with ensuite facilities & 1 BB
  • Luggage transfer
  • Information pack including route notes & maps
  • Emergency hotline

What's Not Included

  • Dinners, lunches & beverages
  • Mountain Bike or Hybrid Bike hire - 120 EURO, E-Bike hire - 180 EURO
  • 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


Duration:7 Days
Starting Point:Siena
Finishing Point:Montepulciano
Activities:Self-Guided Cycling
Grade:moderate to challenging  Click for more information
Trip Code:CST
Prices From:GBP£1030 Per Person