Walking South of Siena

Walking South of Siena information and booking

  • Duration
    8 days
  • Group size
  • Difficulty
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Schedule Details

  • 7 nights hotel


  • Hiking Through Classic Tuscan Landscapes
  • Convents, Cloisters and Medieval History
  • Famous Vineyards
  • Hot Springs at Bagno Vignoni

Tour description provided by World Expeditions

This tour is slightly more challenging than our “Treasures Of Tuscany” and it takes you to see the quieter side of the region, to the South of Siena. Starting in this beautiful bustling city, 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.

What's included

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


Day 1 Arrive in Siena
Arrive in Siena by train from Pisa or Florence via Empoli, where you change trains. From the train station the hotel is a 10-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) 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! Overnight Siena. Accommodation: In the lively and sophisticated city of Siena we stay at a small, comfortable town hotel (3 star) in rooms with en suite facilities, telephone and TV.
Day 2 Siena to Taverne d'Arbia (25km, 15.5 miles/6 hours)
Take a bus from Siena to Taverne d’Arbia (20 mins). It's then an approx 25km/15.5 miles, 6 hours 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. Accommodation: Our 3* hotel in Asciano also boasts a small swimming pool and a nice back garden.
Day 3 Asciano to Buonconvento (5h walk, 13.5 miles/22km)
From Asciano you continue crossing 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. Crossing olive tree fields along woodland tracks and white roads, you will eventually 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. Accommodation: In Buonconvento we stay overnight in a renovated 3 star hotel, which is located in the center of the town, or an ultra modern sister hotel in the modern part.
Day 4 Buonconvento to Montalcino (6 hours walk, 12 miles/19.5km)
A general gentle up & downhill walk passing some great villas, e.g. Castelrosi and Castles, e.g. 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! Overnight in Montalcino. Accommodation: In Montalcino our hotel is 3 star rated, all rooms have private bath, TV and telephone. You will get magnificent views and the hotel also has a small swimming pool. This is a wonderful town with lots to do and see and we would recommend an extra night here if you wish to extend your holiday.
Day 5 Montalcino to Bagno Vignoni (7/8 hours walk, 14.9 miles/24km)
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 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 (included is the entrance to the more modern thermal pool, so that you don’t have to go in with the pope!). Extend your stay, after yesterday’s hard walk, relaxing in the baths and walking to S.Quirico & Rocca d’Orcia. Note that the public thermal pool is generally open, but has occasionally been closed due to different reasons and we cannot guarantee its status for the date of your visit. Accommodation: In Bagno Vignoni we stay in a 3 star hotel overlooking the ancient thermal pool. The entrance fee for the thermal bath is included, although you will be asked to buy a swimming cap (E3).
Day 6 Bagno Vignoni to Pienza (5 hours, 14.5km/9 miles)
A steep hill brings you to the village of Vignoni, the view is quite unique. From here you walk on to S.Quirico d’Orcia. A small town surrounded by some 15th century town-walls, topped with 14 turrets. Things to see there 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 it is known for its good “Pecorino cheese”. Pienza, built by Pope Pius II, (Piccolomini), who was born in Siena, is the perfect Renaissance town. Overnight in Pienza. Accommodation: In Pienza we stay in a 3* hotel in, or just out of the town center, which has been restored. Modern room comforts make the stay a high point of the tour.
Day 7 Pienza to Montepulciano (4 hours walk, 8.4miles/13.5km)
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. Accommodation: The last night of our tour in Montepulciano is spent in a family run 3* hotel, there are several we use in the centre.
Day 8 End of tour
Depart Montepulciano after breakfast by bus or taxi to Chiusi then take a train back to Pisa, Florence or Rome.