Guided Walking and Sightseeing at San Quirico d’Orcia

• Our experienced leaders offer the choice of two different walks each day
• Choose the option which best suits your interests and fitness
• We provide flexible holidays. Choose easier walking one day and harder the next or just explore independently or relax around the resort
• Our leaders are friendly and welcoming making your holiday fun and sociable

Easier Walks      Harder Walks

Walks on good tracks and paths, with short but steep ascents to the hill-top towns.

Day 1: Arrival day

For those arriving on the Pisa flights, the onward journey to San Quirico is by coach. You should arrive at the hotel with time to settle into your room, and perhaps explore some of the town on an optional town trail. On the first evening your leaders will explain more about the organisation of the week and the walks and there will be plenty of time to meet with your fellow guests. 

Day 2: Pienza

The town was originally a village named Corsignano and was the birthplace of Aeneas Piccolomini who later became Pope Pius II. It was he who renamed the village Pienza and in 1459 commissioned an architect to create a Utopian new town. Construction took 3 years and included a cathedral, papal palace, town hall and residences for bishops and cardinals. Pius died just 2 years after the building work was finished and his dying wish was that the buildings should be left unchanged. The result is a unique example of consistent Renaissance architecture.

Both walks will leave from the hotel.  From the walls of San Quirico we will get a glimpse of Pienza, our destination. We head out through the gates of the town heading east to cross the valley of the Fasso Rigo. We walk on tracks and traditional Tuscan “white” roads, finally ascending to Pienza with ample time to explore and take refreshments before we return to the hotel by coach.

Easier Walk: 6 miles with up to 925 feet of ascent

Harder Walk: 7½ miles with up to 1,040 feet of ascent 

Day 3: A View from the Rocca 

Today we take transport south to the castle keep of Tentennano, known locally as Rocca d’Orcia. Early historical documents show a fort here as early as 853AD which gradually became more important until in the 12^th century when it was owned by the Tignosi family, who lost it to the powerful Salimbeni family from Siena. They in turn lost it to the city of Siena during a rebellion in 1419.  It was then incorporated into the line of defensive towns marking the southern boundary of the Republic of Siena.

Close by is the town of Castiglione d’Orcia which also has a castle. Both walks are circular starting and finishing at the Rocca.  We will walk through undulating farmland and woodland where wild game such as deer and boar have been seen, with excellent views of the forested slopes of Monte Amiata in the distance. At the conclusion of the walk there will be the opportunity to climb to the top of the keep and see one of the most spectacular views in Tuscany, or visit the nearby village.

Easier Walk: 5¾ miles with up to 914 feet of ascent

Harder Walk: 9½ miles with up to 1,750 feet of ascent 

Day 4: Siena - full day excursion

The city of Siena is a magnet for visitors to this region of Italy. Within its medieval walls lies a stunning collection of beautiful buildings. We will make the 1 hour journey from San Quircio by coach.

At the heart of the city lies the Campo, where the famous ’Palio’ horse race takes place. The surrounding central core is entirely medieval in plan and appearance. The 320ft Torre del Mangia bell tower dominates the scene and it is possible to ascend its many steps to get a bird’s eye view over the city.

The Museo Civico is the Palazzo Publico contains 13^th century frescoes by Simone Martini and the Lorenzetti brothers. In the Piazza del Duomo, the Museo dell Opera is worth a visit. This houses elaborate frescoes and works by Simone Martini and an unusual work of art – the Maesta, a huge altar piece painted by Duccio in the 1270s. An additional bonus if you go into the museum is being able to ascend the ‘new nave’, arguably a better viewpoint than the more famous Torre del Mangia.

The Duomo itself is incredible both inside and out. The black and white marble decoration, the unique marble floor panels and sculptures are all breathtaking. While the Duomo will be very crowded, a far quieter place to visit is the Ospedale of Santa Maria Della Scala, located across the square. It has only recently been converted into a museum. The church itself (admission free) is very airy and then inside the old hospital is a wonderful cycle of frescoes, which depict entirely secular scenes and are described in English.

As well as visiting these principal sights there will also be opportunities to relax in one of the pavement cafés, or to take a wander through some of the city’s quieter corners before the return to San Quirico. 

 Day 5: Montepulciano

Montepulciano is the highest of the Tuscan hill-top towns, being built on a limestone ridge at approx 2,000ft (605m) above sea level. The town is encircled by walls and fortifications, within which lie a wealth of Renaissance churches and palazze. At the heart of the town, at the highest point of the ridge, lies the Piazza Grande or main square. From here it is possible to climb to the balcony of the Palazzo Communale. The town’s wealth largely comes from the wine industry which is based on the famed Vino Nobile. 

The day starts with short coach journeys to Pienza or Monticchielo. Both groups then walk east across rolling countryside towards Montepulciano.  As we approach the town we can stop to visit the pilgrimage church of San Biagio which sits on a grassy platform below the walls. This Renaissance gem was built in 1518 from cream coloured travertine and is well worth a visit. The walks conclude with a steady ascent to Montepulciano. There will be time for sightseeing and sampling the local wines (or taking other refreshments) before returning to San Quirico by coach.

Easier Walk: 5¾ miles with up to 975 feet of ascent.

Harder Walk: 9½ miles with up to 1,595 feet of ascent 

Day 6: Free day

Each week there is a free day when no guided walks are offered. This is an ideal opportunity to relax around the hotel, walk independently, or visit local places of interest.

San Gimignano is a fascinating hill-town with a breathtaking skyline of towers. Upon arrival we can enter the town through the Porta S. Giovanni and then head to the Piazza del Duomo. The Duomo has an exotic interior containing fresco cycles of the Old and New Testament stories. It is worthwhile to visit the Rocca and ramparts which offer extensive views across the countryside. The church of St. Augustine is well away from the crowds and has frescoes on the life of Saint Francis. 

On the return to San Quirico a stop could be made at the heavily fortified small town of Monteriggioni which was once the border of the Florence and Siena republics.

Assisi: This beautiful city is dominated by its Basilica and is famous as the birthplace of St Francis. The Basilica consists of the upper church which is the setting of the world famous Giotto cycle of frescoes on the life of Francis, the lower church with its frescoes by Lorenzetti, and below that the crypt containing the tomb of St Francis.

A visit to Assisi could be combined with a stop at Cortona a very fine hill top town with commanding views. A short walk could take you to the Piazza della Republica, then to the Piazza Garibaldi, from where there is an extensive view looking across Lago Trasimeno.

Both these options involve hiring a coach and there needs to be a significant number of guests interested to make the economics worthwhile.  Alternatives include:

• Visiting the nearby Villa La Foce and its Gardens, made famous by Iris Origo’s book War in the Val d’Orcia – An Italian Diary
• Visiting the hot springs at nearby Bagno Vignoni on foot or on the local bus. These have been known since the Etruscan era and were developed by the Medici family.

Day 7: Montalcino

From our hotel the distant prospect of Montalcino, across the undulating clay hills, attracts the eye. The morning sun colours the huge outcrop whereas, at night the lights shine brightly as a beacon. Montalcino is a Tuscan hill town with a full circuit of walls. It was permanently settled in 1000AD by the fugitives from the Saracens and their family groups – the Borghetto, Pianello, Ruca and Travaglio – defined the four quarters of the town. To this day rival flags hang outside the houses and the groups compete against each other in archery competitions. At the heart of the town lies the Piazza del Popolo, set beneath the medieval tower of the Palazzo Civico. 

Our walks head through forests, vineyards and farmland to the south and west of Montalcino heading for the Abbey of San Antimo.  We will have the opportunity to look around this most picturesque of abbeys and (if the timing is right) hear the monks singing mass. Finally we will head for the nearby village of Castelnuovo dell’Abate where we can take refreshments in one of the local cafes and/or walk up into the mediaeval heart of the village before the return coach to San Quirico.

Easier Walk: 6¼ miles with up to 625 feet of ascent

Harder Walk: 8 miles with up to 775 feet of ascent

Please note that the itinerary outlined is provisional and could be subject to change. A finalised itinerary will be available at the resort and your leader will brief you every evening about the next day's walk.

Local transport 

On some days the walks start and finish at the hotel. On other days we’ll use the hired transport to explore the surrounding area. The cost of transport to and from the walk is payable locally.