Hilltown Gems of Southern Tuscany

Exploring the walls and walking the town of Montalcino
2.0 hours easy strolling
Welcome dinner provided

We arrive from Florence with enough time to walk the walls and discover the piazzas, the churches, the lanes and begin to understand the life of the Montalcinese. Our walk takes us past ancient chestnuts, some still reflecting the impact of the French and Spanish invaders of the 16th century wars, and impressive vegetable gardens that kept the town alive through these wars and are still serving the community and restaurants today.

Montalcino to Buonconvento
5.0 hours easy to moderate
Picnic lunch provided

Leaving via Porta Burelli, the shady gravelled track winds down to the valley floor passing ancient stone walls and the best of the Brunello producing vineyards.

We enjoy the expansive views over rolling hills with broad acre farming and vineyards. Original two-story stone fattorias (farm buildings) dotted on the landscape, accompanied by the silhouette 12 of Tuscany’s famous cypresses are never far from view. At times herds of milking sheep, tendered by shepherds, can also be seen.

After leaving the small hamlet of Bibbiano, we walk through fields with two ancient towers on the horizon keeping watch. The path takes us through a cool forest to reach a road lined with umbrella pines leading us into Buonconvento. Time is then available to explore this historic walled town.

Finally, we visit a small but informative museum that recreates the life under the Mezzadria system, reflecting the centuries of great hardship experienced by the peasants working under a form of feudal system. A system still in place up until the 1950’s.

A local bus will then take us back to Montalcino for a well earned rest.

Montalcino to Abbazia di Sent’ Antimo
2.5 hours easy
Dinner provided

Leaving Montalcino via the fortress, our path passes through a shady forest and crosses small streams before emerging onto quiet laneways and passed old farmsteads, untouched by the years. From here the view back to Montalcino can be enjoyed.

Our path then climbs steadily through open pastures with views over the Val d’ Orca. The hamlet of Villa A Tolli sits isolated with its fountain, cypresses and wooden cross.

Returning to light forest, the path steadily descends to reach the magnificent Romanesque Abbazia di Sant’ Antimo. It has been described as one of the best examples of abbeys in Tuscany, if not all of Italy. Built on the Via Francigena, the pilgrim path from northern Europe to Rome, the abbey provided shelter and sustenance to these pilgrims.

Montepulciano to Pienza via Monticchiello
4.0 hours easy to medium with some steady hill climbs
Lunch at a trattoria in Monticchiello

The highlight of this walk is the opportunity to visit three magnificent hill towns. We walk through pastures that are the source of the famous pecorino cheeses. The wild herbage in the pastures provides this famous cheese with much of its unique flavour. At times, small herds of sheep for milking will be seen grazing along with goats. Sometimes, buffalo are also out grazing from their barns.

An early start is needed to catch the local transport to the fortress town of Montepulciano, home of Vino Noble di Montepulciano. This late Etruscan settlement is set on a high rocky ridge surrounded by superb countryside. After taking time to explore the town, our walk takes us past the stark domed San Biagio and 13 through laneways of small land holdings.

Our walk affords us panoramic views before reaching the tiny fortified hill town of Monticchiello for a hearty lunch.

Throughout the afternoon our final destination of Pienza is almost always within sight. The track is undulating with again large expansive views over broad acre farming and the sheep, goats and buffalo that are famous in this area.

Pienza was created by Pope Pius 11 as the ideal Renaissance town in the 15th century. Laid out by Bernardo Rossellino it remains in remarkably good condition and has been the scene of numerous movies including ‘Room with a View’ and ‘Romeo and Juliet.’

After time to explore the town, our return to Montalcino is via private transport.

Montalcino to San Quirico d’Orcia
3.5 hours easy

This undulating walk through open farm land with good views takes us to the old town of San Quirico d’Orcia. As we walk down from Montalcino views of the fortified hill towns of Pienza and Monticchiello, previously visited, can be seen. The vineyards of Brunello soon give way to pastures of sheep producing the famous pecorino cheese.

San Quirico d’Orcia is a small medieval town dating back to the 8th century on the Via Francigena. It was enlarged in the 13th century to accommodate the pilgrims on their way to Rome.

Bagno Vignoni to Castelnuovo dell' Abata
4.0 – 4.5 hours easy to moderate with three steady hills
Picnic lunch provided
Dinner provided

Private transport will take us to the spa baths of Bagno Vignoni whose waters have been “taken” since Roman times. Before heading off for the day, there is time to explore the large piscine or pool, constructed by the Medici and the perfectly preserved piazza.

Our walk takes us past the caves below the baths where the water was tapped for milling. Old grinding stones are still evident.

We then follow the River Orcia with tremendous views of Rocca d’Orcia and Ripa d’Orcia. Upon leaving the river, the path takes us towards the gates of Ripa d’Orcia, now a fattoria run by a wine 14 producing family. Mount Amiata is often in our view, towering over the surrounding countryside.

After crossing a tributary of the d’Orcia the path enters another valley that has extensive vineyards. At vintage, the aroma of grapes is always in the air and every back lane is busy with tractors ferrying the harvest.

The track slowly winds its way down to Castelnuovo del Abata, along a path shared with porcupines judging by the occasional quill that can be found. These farm tracks are often still lined with squared off stones from the ancient medieval Roman roads.

Our walk concludes with a cool drink at the trattoria as we await our local piccolo bus back to our hotel.

Bus to Florence and to points beyond