Hilltown Gems of Southern Tuscany

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montalcino

Montalcino is a 12th century walled town commanding a magnificent position. On approach the dramatic fortress, built by the Sienese republicans in the 14th century as protection against the Florentines, stands out boldly on the horizon. This is is our home for 7 days of exploring a region rich in history, expansive scenery, the finest fortress hill towns and a centuries old spa town.

Our accommodation for the week is a three-star family run hotel situated inside the walls close to central piazzas. Although operating as a hotel over many centuries, our rooms have been recently rejuvenated with every modern facility yet retain their original charm and atmosphere.

The surrounding hill towns of Montepulciano, Pienza, Monticchiello, San Quirico d’Orcia and Castelnuovo dell' Abata combine to create a feast of exploring possibilities over the coming days.The strong vibrant community of Montalcino is based on the famous Brunello wine, produced only in the surrounding region and considered one of Italy’s finest. Pecorino cheese and honey are also local specialities.


Day 1

Exploring the walls and walking the town of Montalcino
2.0 hours easy strolling Walk
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.

Day 2

Abbazia di Sent’ Antimo to Montalcino Walk
3.0 hours easy to moderate
Dinner provided


We begin our walk at 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.

Our path then climbs steadily through light forest with occasional views over the Val d’ Orca. We reach the hamlet of Villa A Tolli sitting isolated with its fountain, cypresses and wooden cross. Our pathway passes an Etruscan dig where we take time out to explore this interesting site. From the quiet gravel road we enter shady forest pathways which wind back into the outskirts of Montalcino.

Day 3

Montalcino to San Quirico d’Orcia
3.5 hours easy
BYO lunch or try a local café


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.

San Quirico d’Orcia is a small medieval market town dating back to the 8th century. The village grew in the 13 century as it was a resting place for pilgrims walking along the Via Francigena to Rome. You are still able to enter the ancient courtyard of one on the hospices. We will take time to explore this historical town before our private transport takes us back to Montalcino.

Day 4

Montepulciano to Pienza via Monticchiello
4.5 hours moderate 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. At times, small herds of sheep for milking will be seen grazing along with goats. 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 through laneways beside small land holdings.

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

Day 5

Buonconvento to Murlo Walk
4.5 hours easy
Picnic lunch provided

By now you will be fully immersed in the beauty of Southern Tuscany’s landscape. This special walk takes us past and through cultivated valleys, tiny hamlets, into a nature reserve and finishing in the pretty hamlet of Murlo.

Our walk starts in Buonconvento with time to explore this historic market town. After leaving Buonconvento we walk through cultivated fields and small hamlets taking a short detour to visit the foundations of a small Roman villa from 1BC. We continue on a pathway through a nature reserve and into Murlo. Murlo has an excellent Archaeological Museum. Our return to Montalcino is via private transport.

Day 6

Bagno Vignoni to Castelnuovo dell' Abata
4.5 hours 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 producing family. It is fantastic to approach Abbazia di Sent’ Antimo on foot. It is an unforgettable sight to first see this Abbey below you tucked into the most beautiful surrounds.

We arrive in time to attend the 2:45 pm service at the Sant’ Antimo Abbey. This very old and beautiful Gregorian chant by the community of cannons lasts approximately 20 minutes.

Day 7

Bus to Florence and to points beyond.


Our three dinners include...


  • * Tuscan simplicity, excellent local produce and a good kitchen. Enjoy traditional Tuscan vegetable soup, pici or may be Tuscan pork sausage with white beans complimented with a glass of Rosso.
  • * Dining at a local trattoria.  Settle in for a relaxed evening in this rustic trattoria with its, good southern Tuscan cooking.
  • * The restaurant for our farewell to Montalcino is splendid.  The menu is modern Italian and exquisite.

Tour Dates :

May 21st – 27th 2010

September 24th – 30th

Tour Price:

$2,600 twin share
Includes all breakfasts, 3 lunches, 3 dinners, two guides and all transportation from Florence, local transport, entrance & wine tour fees as per itinerary.
Not included are wines and other beverages with alcohol.
Note: A supplement of $500 applies for a single room
Special Offer: If you book two walks back to back a 10% discount applies