Arrival to your first accommodation in Montepulciano. Spend some time strolling around this beautiful town, with its many Renaissance palazzi and churches.
Walk to the beautiful church of San Biagio on the outskirts of town, then head into the countryside. Stop at the walled village of Montichiello for lunch or an espresso 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.(15 km distance/490 m total elevation gain)
Continue through a beautiful region of rolling hills, oak woods, and charming villages. Pass through
San Quirico d’Orcia (409 m), another walled city with an elegant 12th century church and Bagno Vignoni, a spa town which has central square that has a huge steaming pool of sulfurous water famed for its healing properties since Roman times. End the day in the tiny cillage of Rocca d’Orcia. (21 km/685 m total elevation gain)
On this challenging day, you will walk along dry riverbeds to reach the isolated Abbazia de Sant’Antimo, with its magnificent Romanesque church which the locals like to say was founded by Charlemagne in the 8th century. There are 10 more km to go before you get to today’s destination, Montalcino, so you’ll be picked up at the abbey and driven the rest of the way. (13 km/585 m total elevation gain)
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 night at a delightful agriturismo near Buonconvento.(23.5 km / 525 m total elevation gain)
Enjoy a leisurely day relaxing around the pool or follow a hilly path to the 14th-century Benedictine abbey of 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 back from the abbey takes 3 hours.
(10 km/255 m, beginning with a shuttle to Monte Oliveto Maggiore)
Walk along a winding dirt road over hills and through oak woods. Pass buenconvento and 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. You’ll be met in Murlo and transferred to Siena.
(16 km/285 m total elevation gain)
Enjoy the sights of Siena before your departure. Stroll through the Piazza del Campo and to the spectacular Duomo, one of the few full Gothic Cathedrals built south of the Alps.