Day 1 – Acquaviva to Montepulciano (3 hours walking time)
Arrival in Chiusi where you are met by our Italian representative who will spend a short time going over the tour with you answering any question you may have. (The train takes about an hour and a half from Rome and trains operate every 2 hours throughout the day. See travel information below.) Our representative will then drive you to Acquaviva where the trail to Montepulciano starts. Hotel in Montepulicano, one of Tuscany’s highest hilltop towns. Renowned for its Vino Nobile, Montepulciano also boasts a unique blend of Renaissance architecture and is perched on a narrow ridge of volcanic rock.
Day 2 – Montepulciano/Pienza (6 hrs walking time)
From the church of San Biagio on the outskirts of town, you will follow an old road through the countryside. Stop at the walled village of Montichiello for lunch or a cappuccino before making your way to Pienza, a small town once called “the pearl of the Renaissance”. Partly redesigned by Pope Pius II, Pienza boasts a splendid Renaissance cathedral and the charming Palazzo Piccolomini. Sample pecorino, a local sheeps’ cheese.
Day 3 – Pienza to Bagno Vignoni (5 hrs walking time)
The walking today crosses a beautiful region of rolling hills, oak woods and lovely villages. Your destination tonight is Bagno Vignoni, a thermal spa town where the main square is a basin of steaming hot water. This is considered by many to be the most charming village in all of Tuscany! Hotel in Bagno Vignoni.
Day 4 – Bagno Vignoni to Sant’Antimo/Montalcino (5 hrs walking time)
Today’s walk takes you along dry river beds in a rather wild environment to reach the Abbey of St Antimo. Few of the monastic buildings remain, but the 12th-century church is well preserved and is an outstanding example of the Italian Romanesque. With luck, you’ll visit at a time when the monks celebrate mass and the church echoes with Gregorian chants. We’ll arrange to have you transported from the Abbey to Montalcino, your home for the night.
Day 5 – Montalcino to Buonconvento – (4 hrs. walking time)
Montalcino is renowned for its ruby-red Brunello wines, so you’ll spend much of the day strolling through vineyards as well as olive groves. Then you’ll enter the primeval landscape of the crete senesi , where shepherds tend the sheep whose milk is used to make pecorino cheese. Spend the next 2 nights at a delightful inn near Buonconvento.
Day 6 – Buonconvento Loop (3 hrs. walking time ONE WAY)
Enjoy a leisurely day relaxing around the pool or follow a hilly path to the 14th-century Benedictine Monte Oliveto Maggiore, one of the most impressive abbeys in Italy. Contemplate the cloister with its magnificent fresco cycle on the life of St. Benedict. The walk to the abbey takes 3 hours and if you prefer not to walk back to your inn, the owner of your accommodation will come and pick you up.
Day 7 – Buonconvento to Siena – (5 hrs walking time)
Walk along a winding dirt road over hills and through oak woods. Pass Murlo, a tiny medieval borgo, the oldest settlement in the area. A ring of houses forms Murlo’s defensive walls. Visit the Museo Etrusco, which commemorates the town’s Etruscan origins. Then on to Radi and Monteroni d’Arbia, where we will arrange a transfer to Siena
Day 8 – Departure
Your tour ends after breakfast, but you will want to enjoy the sights of Siena before your departure. Stroll through Piazza del Campo and to the spectacular Duomo, one of the few full Gothic cathedrals built south of the Alps. There are both train and bus stations in Siena with easy access to both Rome and Florence. You might also choose to spend an additional day in Siena as there is so much to see here.