Walking South of Siena

Walking on the Crete SenesiWalking up to the Crete SenesiBagno VignoniPalzzo Pubblico, SienaTowards PienzaSanta Antimo

Walking South of Siena

Trip Highlights

  • Hiking through classic Tuscan landscapes
  • Convents, Cloisters and Medieval History
  • Famous Vineyards
  • Hot Springs at Bagno Vignoni

Trip Summary

Starting in the beautiful bustling city of Siena, you head off into a coffee table book Tuscan landscape of gentle hills, tipped by a lonely pine or Holm oak tree while cypresses line the way leading to the distant farmhouses. From the outskirts of Siena, the first walk takes you along the undulating ‘Crete Senese’ chalk downs to the mediaeval town of Asciano. Perfectly proportioned like a miniature Siena. The next day, back on the ‘Crete,’ you pass by one of the most beautiful 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 for the famed Brunello wines, as far as the walls of Montalcino offering breathtaking views. Another peaceful walk takes you to the St.Antimo Abbey a unique structure in pure Romanesque style where the prayers and songs of a community of French Gregorian friars echo throughout the cloisters. Then it is off along more cypress lined roads and forests to discover the hot springs used in Renaissance times by Lorenzo dei Medici and by Popes at Bagno Vignoni, where there is a huge pool of healthy sulphurous water where normally there would be a town square. The next day the walk passes through the small town of San Quircio with its clipped renaissance gardens, before ascending to Pienza a creation by Pope Pius II, largely completed within three years. Our tour finishes in the city of Montepulciano where medieval architecture and vineyards line the landscape, as we enter the wine lands of Nobile de Montepulciano.


Clients should have a reasonable level of fitness and should be able to walk for up to 5-7 hours a day in hot sun on dusty or stony tracks; a couple of days are around 25km. There are a couple of cross country sections lasting between 1.5 and 2.5 km where care is needed to follow route notes, as you will be crossing farmland.


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, called Hotel Minerva.

Meals:  Nil

Take a 20 minute bus ride from Siena to Taverne d’Arbia. Today you will be walking through Crete Senesi to Asciano. You will have some views back on the city as you arise through a string of hamlets in a largely sheep farming area, before you undulate along to Asciano, a tightly packed mediaeval walled town with Sienese architecture. Total Ascent: 741m/Total Descent: 668m Accommodation: The Agriturismo Dipinture has 4 beautiful spacious rooms.

Meals:  B

From Asciano you continue crossing 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. Crossing olive tree fields along woodland tracks and white roads, you will reach the small town of Buonconvento, where the Emperor Henry VII died in 1313. The old section has a perfect embrace of walls, and there are little alleys running off the main street waiting to be explored. Total Ascent: 654m/Total Descent: 711m Accommodation: Hotel Il Ghibellino is a a 3 star hotel, which is located in the centre of the town.

Meals:  B

A general gentle up & downhill walk passing some great villas and castles including Bibbiano. You will then cross the Ombrone River and come into the wine producing area of Brunello de Montalcino. The last part of the walk will lead you up to Montalcino, a 328m climb. The walk is steep but panoramic and reaching the gate in the town-walls, it will feel like a conquest! Total Ascent: 670m/Total Descent: 285m Accommodation: Hotel Dei Capitani is a 3 star hotel. 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

This is the hardest walk, crossing one of the most remote areas. Today you have a long downhill walk to the Romanesque 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. Total Ascent: 867m/Total Descent: 1068m Accommodation: Il Loggiato BB dates back to the 13th century, it has 6 rooms so has that lovely personal feel to it.

Meals:  B

A steep hill brings you to the village of Vignoni where the view is quite unique. From here you walk on to S.Quirico d’Orcia. A small town surrounded by 15th century town-walls, topped with 14 turrets. Things to see here include the 13th century Romanesque Collegiate Church, with the “Horti Leonini” - an unusual Italian-style garden. To reach Pienza your walk crosses open countryside. Instead of the vineyards, many sheep populate this area that is known for its good “Pecorino cheese”. Pienza, built by Pope Pius II, (Piccolomini), who was born in Siena, is the perfect Renaissance town. Total Ascent: 606m/Total Descent: 411m Accommodation: Hotel La Valle is another 3* hotel.

Meals:  B

A gentle up & downhill walk to reach Montepulciano, another wine area. On the way you can stop at Montichiello, 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. Total Ascent: 649m/Total Descent: 523m Accommodation: The last night of our tour is spent in the family run Albergo Duomo a 3 star hotel.

Meals:  B

Depart Montepulciano by bus or taxi to Chiusi then take a train to Pisa, Florence or Rome.

Meals:  B

What's Included

  • 7 breakfasts
  • 5 nights accommodation in 3 star hotels, 1 Agriturismo, 1 BB on a twin share basis with ensuite facilities
  • Luggage transfer
  • Information pack including route notes & maps (1 pack per room booked)
  • Emergency hotline

What's Not Included

  • Dinners, lunches & beverages
  • 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:8 Days
Starting Point:Siena
Finishing Point:Montepulciano
Activities:Self-Guided Walking
Grade:moderate  Click for more information
Trip Code:JST
Prices From:GBP£1160 Per Person
Single Supplement:GBP£500  Click for more information
Solo Traveller:GBP£740  Click for more information
Please do not book any flights or extra arrangements until such time that your booking is confirmed by Sherpa Expeditions by phone or email.