Sherpa Bike Rides: Cycling South of Siena

Tour code: CST
Revised: October 2007

This more challenging cycling tour than our original Tuscany tour, 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 Castiglion del Lago. Situated on a small promontory on lake Trasimeno. This fortified town is still surrounded by its ancient walls and its distance from the modern residential zone keeps it unaltered. It is now one of the most important tourist centers around lake Trasimeno. It was near here that in 217B.C Hannibal defeated a huge Roman army.

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 5minute 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 mediaeval 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. Distance 58km

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

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.

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 mediaeval 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. Distance: 45km

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 mediaeval town of Montepulciano. This has one of the most impressive renaissance buildings in Italy: the church of San Biagio

Distance: 47km

Day 7: Montepulciano – Castiglion del Lago. An easy cycle ride today which will lead you down to the fortified town of Castiglion del Lago which is still surrounded by its ancient walls and its distance from the modern residencial zone keeps it unaltered. First a town of fishermen then an agricultural area, Castiglione del Lago is now one of the most important tourist centers around Lake Trasimeno. Distance 39km

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 flies direct to Pisa from London Stanstead, and Glasgow airport using their flights you could make a considerable saving on your holiday.

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 90 Euros) directly to Siena. 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

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 78 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. You are advised to bring your own cycle helmet.

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. 1) 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. 2) You are not just paying a supplement on the room but the luggage transfer costs you are paying in full. The cost of moving 1 bag or 2 bags etc remains the same. On some of our trips it is possible to reduce the cost of the single supplement if you happen to be a 3^rd person travelling, or have chosen a date when other clients are booked.

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.

Luggage: When staying in hotels, sometimes your luggage will have been taken to you room awaiting your arrival. However don’t be surprised if your luggage is waiting for you to take it up to your room.

Accommodation & Meals

Accommodation is on a bed and breakfast basis in comfortable hotels with en suite facilities when available. 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 en suite 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 spend our night in a pleasant "Meuble" (hotel without restaurant) located in a renovated medieval hospital.

Night 7: In Castiglion del Laga we stay in a comfortable room rental that has a really nice view overlooking Trasimeno Lago. From here there is the opportunity of a ride to the magnificent medieval town of Cortona; we advise that you extend your stay for an extra night in order to do this.

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