This 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 mediaeval 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 mediaeval 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 when you get there. Our tour ends in Cortona near lake Trasimeno where in 217B.C Hannibal defeated a huge Roman army. Cortona is yet another fascinating medieval hill town with steep narrow streets, a delightful square and interesting churches such as Santa Maria delle Grazie, built in 1484-1515 to house the ‘miracle-performing image’ of the Blessed Virgin Mary, the "Madonna del Calcinaio".

Outline Itinerary

Day 1: Arrive in Siena by train from Pisa or Florence via Empoli, where you change trains. From the train station the hotel is a 15 minute walk or you could take a local taxi available in front of the station (not included). You can travel by bus from Rome or Florence. If you arrive at Rome Fiumicino airport take the train to “Roma Tiburtina”. In front of the station from the bus terminal, take the “Sena” bus for Siena. In Siena get off at Piazza Gramsci. The hotel is a 5 minute walk.

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), 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. Overnight Siena.

Day 2: Siena to Buonconvento. Our first cycling day is through the Chianti hills. From here you cross the fascinating area of hills called the Crete Senesi and you reach 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. Even the library and the church of the convent are architectural masterpieces. You then continue on until you eventually reach the small town of Buonconvento, where the Emperor Henry VII died in 1313. Quite a tough day. Distance 58km, there is a 'medium' route alternative 42km.

Day 3: Buonconvento to Montalcino. Today you will pass some great villas, e.g. Castelrosi, Castles, and Bibbiano. 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 25km mixed surface ride.

Day 4: A free day in Montalcino either relaxing by the pool or alternatively a ride to visit the village of S 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. 41km mixed surface ride of medium difficulty.

Day 5: Montalcino to Bagno Vignoni. Today’s cycle ride will take you to the romanic 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 we 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. Overnight in Bagno Vignoni. Medium/difficult route mainly on gravel roads. Distance: 34km. Easier tarmac road option 33km.

Day 6: Bagno Vignoni to Montepulciano. Cycling through open countryside that will lead us to a Renaissance jewel, Pienza. Built by Pope Pius II, (Piccolomini), who was born in Siena. We cycle through the small pleasant village of Monticchiello, a surprising small village located on the top of a hill with a marvellous 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 27.5km option available.

Day 7: Montepulciano – Cortona. An easy cycle ride today, which will lead you down to and around Lake Trasimeno, then up to Cortona. Distance 45km

Day 8: End of tour by bus or train back to Pisa, Florence or Rome.

Extra nights

Siena is certainly a beautiful city, yet despite its size, it has something of a village feel to it. There is so much to see and so many good places to eat that it is worth an extra day. We can arrange extra nights here or in Florence which is only about an hour away by bus from Siena.

On Self Guided Tour we provide you with:

Route notes, maps at 1:25.000 scale. 

Travel Information

Travel: Our air travel package price includes the flight to Pisa using the scheduled services of British Airways from London Gatwick to Pisa. Alternatively Ryanair and Easyjet fly direct to Pisa.

Arrival: The tour starts in Siena, which is easily reached by bus from Rome in 3.5 hours or by train from Pisa, 2 hours, and from Florence in a little over 1 hour.

As an extra service: We can normally arrange an economical transfer to the start of the walk from Pisa (approx 100 Euros) directly to Siena or from Florence (90 Euros). Please note that this transfer is an additional cost and should be pre booked. Payment is made locally in cash.

End of Tour: The tour ends after breakfast on day 8 in Castiglion del Laga. This town is well connected with Chiusi from where, by train you can quickly reach Pisa, Florence and Rome.

Season: April to November bear in mind that July and August can be hot than at other times of the year.

Level of Difficulty

Grade: 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 50kms in hot sun on dusty or stony tracks.

Waymarking:  Most of the route is marked by red/white marks made by the CAI (Club Alpino Italiano) when these are not available you will have to refer to our route notes.

Bikes: Bikes can be hired for 80 Euros per person. This is paid on arrival of your bikes in Siena. The bikes are 24 gears, front suspended Mountain Bikes equipped with lock, panniers and basic repair kit. For hygiene reasons we advise you to bring your own cycle helmet and water bottles.

General Information

Breakfast: in countries such as Italy are usually coffee and toast/croissant, if you want more for breakfast then we would suggest you purchase some food the night before. It is important for you to tell us if you have any dietary requirements when you book your holiday so that we can inform everyone that you are staying with.

Single Supplements: are payable on most of our tours. The single supplement guarantees the privacy of your own room, however, rooms can at times be small and in some places may not enjoy the same facilities as double/twin rooms. 

Language: When travelling in less frequented areas you will not necessarily come across people speaking English. Remember you have left home to find things different so carry an Italian phrase book with you.

Accommodation & Meals

Accommodation is on a bed and breakfast basis in comfortable hotels with ensuite facilities. No evening meals are included, but there are generally plenty of places where you eat each evening. You can normally eat quite well in a Tuscan trattoria for about 25 Euros including a basic wine.

Picnic lunches are not included in the tour price, but materials for picnics can be purchased in each of the towns and villages where you stay or pass through – be careful with the old wines!

Night 1: In the lively and sophisticated city of Siena we stay at a small, comfortable 3* hotel in rooms with ensuite facilities, telephone and colour TV.

Night 2:  In Buonconvento we stay overnight in a recently renovated 3* hotel, which is located in the center of the town.

Nights 3 & 4:  In Montalcino our first choice of hotel is 3* rated, all rooms have private bath, TV and telephone. You will get magnificent views and the hotel also has a swimming pool. This is a wonderful town with lots to do and see.

Night 5: In Bagno Vignoni we stay in a 3* hotel overlooking the ancient thermal pool.

Night 6:  In Montepulciano we use a 3* family run hotel situated in an old Renaissance Palazzo. 

Night 7:  In our 3* hotel set in the historic centre of Cortona, making it easy to access all the places of interest.

PLEASE NOTE: It is generally normal practice when staying in hotels that you check-in at or after 2pm and checkout by 10am the following morning. Guesthouses/bed & breakfast establishments are normally check-in at or after 4pm and checkout by 10am.