Classic Trails of Tuscany: Siena to Montepulciano – 8 Days

On arrival to Siena, head to the dramatic Piazza del Campo. Formerly the meeting point of 3 major routes in and out of Siena, the piazza was developed as a neutral meeting ground where political holidays and festivals could be staged. A unique design said to be in the shape of the Virgin Mary’s cloak, the piazza thrives with tourists and twice a year hosts the colourful Palio horse event.

Meals included: None
Accommodation: Hotel Chiusarelli
Start your Tuscan week of walking with a night in a typical neoclassical villa dating back to the 1870s. Located in the historical centre, several years ago the hotel was refurbished to a traditional Sienese house, complete with large, beautiful preserved frescos. A charming and fitting end to your walking trip.

From the magnificent Piazza del Campo, depart Siena on foot as you follow sections of the ancient pilgrim route, ‘Via Francigena’ (which starts in Canterbury, southern England and ends in St Peter’s Square, Rome). The trail heads through the ‘Crete Senesi’ landscape to Monteroni d’Arbia and along with typical ‘Strade Bianchi’ (Tuscan white gravel roads). On arrival at Monteroni d’Arbia, a short, private transfer (10mins) will take you to your rural accommodation in the hills above Buonconvento.

Walk: 21km
Ascent: 160m
Descent: 330m
Meals included: Breakfast & Dinner
Accommodation: Pieve a Salti
Nestled deep in the Tuscan countryside at this agriturismo. Relax poolside, overlooking the countryside or head to the spa for a reviving leg massage. Pieve a Salti is a working farm, run by the Parandi family who cultivate over 700 hectares of land for local produce (much of which you will sample during your stay here).

Begin the day with a short transfer to Buonconvento (10mins) and wander along its historical centre, Via Soccini. Leaving   Continue walking through the iconic Senese landscapes, along trails and strade bianchi (white roads) lined with the towering and elegant cypress trees and through the Brunello vineyards, using Sangiovese grapes for world-class wine. The day ends with a climb up to the 14th-century hill town of Montalcino, nestled amongst the hills of the Val d’Orcia.

Walk: 18.5km
Ascent: 540m
Descent: 3170m
Meals included: Breakfast
Accommodation: Hotel dei Capitani
Dating back to the middle ages, Hotel dei Capitani is believed to have been used as a refuge for Sienese people fleeing the Florentine army. The hotel pool boasts splendid views across Val d’Orcia and Van d’Arbia, which can also be viewed from your room, which have a typical Tuscan decor.

South of Montalcino, an easy-going route, rolls through classic Tuscan landscapes. Just before reaching the delightful town of Castelnuovo dell’Abate, take time to visit the Romanesque Abbey of Sant’Antimo, dating back to the 8th century. The monks at the abbey still meet seven times a day, so you may be fortunate to hear the medieval Gregorian chants. Above the abbey, the village of Castelnuovo is a superb stop for lunch. Later in the afternoon, a private transfer will take you on to the Roman spa town of Bagno Vignoni.

Walk: 12km
Ascent: 280m
Descent: 470m
Meals included: Breakfast
Accommodation: La Locanda Loggiato
Sisters Barbara and Sabrina have been welcoming guests to Bagno Vignoni for almost 20 years. Their 14th century property has been lovingly restored with all en-suite rooms featuring terracotta flooring and traditional wooden beams. A place of relaxation, not all bedrooms have wi-fi (but it is available in communal areas). La Locanda is the perfect environment to relax in after a visit to the thermal baths just a few minutes away in the main piazza.

Begin the day with a rewarding stretch uphill to Vignoni Alto, complete with its own fortress tower. Onto San Quirico d’Orcia, the route gently descends through rich agricultural lands. Located on the Via Francigena pilgrim route, in medieval times the beautifully preserved San Quirico d’Orcia was of significant strategic importance, linking Europe with Rome. Do make time to explore the town and enjoy lunch in one of the many rustic restaurants. Continuing onto the hilltop town of Pienza be sure to try the local Pecorino cheese made from sheep’s milk.

Walk: 19.5km or 15km
Ascent: 660m or 400m
Descent: 600m or 250m
Meals included: Breakfast
Accommodation: Hotel La Valle
Within a couple of minutes of Pienza’s historic centre, the hotel occupies a typical Tuscany stone building. Complete with a roof garden, panoramic breakfast room, bar and en-suite rooms, enjoy breakfast on the terrace with views that stretch out over golden wheat fields and vineyards.

Set across a rolling hilltop, the elegant town of Montepulciano boasts one of Tuscany’s oldest wine producers; Vino Nobile. Walk via the hamlet of Monticchiello through a patchwork of rolling fields as the trail climbs up to Montepulciano. Explore the labyrinth of cobbled streets, lined with elegant Renaissance palaces, former homes of nobility and hidden piazzas. At the heart of the town is Piazza Grande, a wonderful setting to taste the rich variety of Montepulciano wines. In the evening it’s worth strolling out to the edge of the old town and seeing the sunset over the Val d’Orcia.

Walk: 15km
Ascent: 550m
Descent: 450m
Meals included: Breakfast
Accommodation: Hotel Il Rondo
Located outside the lively town centre, the family-run Hotel II Rondo is tucked away in a peaceful corner of Montepulciano. After a day of walking and exploring, relax in the impeccably maintained gardens. In keeping with the period of the building, rooms have been decorated to an 18th-century style.

North of Montepulciano is the delightful hilltop hamlet of Montefollonico overlooking the Val d’Orcia and Valdichianna. A 13th-century walled town, the Church of San Leonardo has become one of the most important examples of Romanesque architecture within southern Tuscany. If you’d prefer an easier day, it is possible to take local transport to Montefollonico or simply head back in the cavernous streets of Montepulciano and further acquaint your palette with the diverse and delicious red wines produced in the region.

Walk: 18.5km (or 9km and return by bus)
Ascent: 665m
Descent: Descent: 665m
Meals included: Breakfast
Accommodation: Hotel Il Rondo

From Montepulciano the nearby train station, Chiusi Chianterme has regular connections through to Florence, Pisa and Siena. You may also have time to further explore the streets or Montepulciano or relax in the garden of your hotel.

Meals included: Breakfast