Tuscany Area Guide

Guide to Tuscany

Tuscany is central Italy's largest region with a population of over 3.75 million. Located on Italy's west coast, Tuscany borders the Tyrrhenian Sea, the Ligurian coast, the Apennine Mountains and the regions of Umbria, Emilia-Romagna and Lazio. Tuscany includes a range of coastlines, coves, valleys, hills and mountains. The rich soils produce world famous wines and the Alpi Apuane of the northwest are home to the renowned Carrara marble quarry.

Tuscany is seen as the essence of Italy in many ways; an idyll of olive groves, vineyards, hill-towns and frescoed churches. The national language evolved from the Tuscan dialect, a supremacy ensured by the Florentine Dante (who wrote the Divine Comedy in the vernacular of his birthplace) and other Tuscan writers such as Petrarch and Boccaccio. The Renaissance, which played so large a role in forming the culture, not just of Italy but of Europe, is associated more strongly with this part of the country than with anywhere else.

Florence was the hot-bed of the Renaissance, flourishing principally through the all-powerful patronage of the Medici dynasty. Every eminent artistic figure from Giotto onwards – Masaccio, Brunelleschi, Alberti, Donatello, Botticelli, Leonardo da Vinci, Michelangelo – is represented here, in an unrivalled gathering of churches, galleries and museums.
If Florence is primarily about the Renaissance, in Siena it's the medieval period that predominates and it remains almost perfectly preserved. Here the city itself is the great attraction and you can have a wonderful time without setting foot in a single museum. The scallop-shaped Piazza del Campo is arguably the most beautiful public space in all of Italy whilst the duomo is one of the country's mightiest monuments.

Pisa has much more to offer than just the leaning tower, which is certainly remarkable, but it is just a single component of the amazing Campo dei Miracoli, where the Duomo, Baptistery and Camposanto complete an unrivalled quartet of medieval masterpieces.  Nearby Lucca, on the other hand, is graceful with a largely traffic-free centre that's strewn with handsome buildings; you can hardly walk for five minutes without coming upon a small piazza and marble-fronted church facade.

Tucked away to the west and south of Siena, dozens of small hill towns epitomize the region for many visitors. San Gimignano is worth visiting as much for its spectacular array of frescoes as for its bristle of medieval towers.

Volterra, west of San Gimignano sits on a windswept plateau enclosed by volcanic hills and was described by D. H. Lawrence as "a sort of inland island," and it does have an air of being somewhat cut off from the rest of the region. Like Cortona, it was a major Etruscan settlement, and the town's museums are stuffed with relics of that enigmatic civilisation.

The Val d’Orcia (or Valdorcia) extends from the hills of Siena to Monte Amiata. It is characterised by carefully cultivated hills punctuated with picturesque towns and villages such as Pienza, Radicofani and Montalcino. It is a landscape which has become familiar through its depiction in art from Renaissance paintings to modern photographs and became a world heritage site in 2004.
Areas we cover in the province of Siena


Asciano is located at the centre of the ‘Crete Senesi’ some 30 kilometres south-east of Siena. Asciano has evidence of Etruscan, Roman and Lombard settlements; an Etruscan necropolis dating back to the 5th century BC has been excavated nearby and the remains of Roman baths with fine mosaic paving were uncovered in the town in 1898. During medieval times the site was fought over by Siena and Florence at the battle of Montaperti in 1260; part of the centuries long conflict between the Guelphs (supporters of the Papacy) and the Ghibellines (supporters of the Holy Roman Emperor). Some twenty years later it was purchased by the Sienese and surrounded by walls in 1351. The village has some 14th-century churches with paintings dating back to that period. There is also the travertine-built 11th century Romanesque basilica of Sant’Agata that has a 13th century bell tower. The basilica houses two 16th century frescoes; a Pietà by the above mentioned ‘il Riccio’ and another by Giovanni Antonio Bazzi, who was also known as ‘Il Sodoma’, a nickname that he clearly didn’t find upsetting for some reason. Adjoining the church is the museum of sacred arts and there is also an archaeological museum.
10 kilometres further south there is the Benedictine abbey of Monte Oliveto Maggiore which was founded in 1320 by Bernardo Tolomei of Siena. The cloister is famous for a series of frescoes that were initiated by Luca Signorelli and completed by ‘il Sodoma’ in 1505. The church also contains fine inlaid choir stalls by Fra Giovanni de Verona.


Buonconvento is in the Crete Senesi about 70 kilometres south of Florence and 25 southeast of Siena. The name comes from the Latin ‘Bonus Conventus’ which means ‘happy place’ and is mentioned for the first time in 1100. In 1313 Henry VII, the Roman emperor, died there.  It became part of the Grand Duchy of Tuscany in 1559 until it was annexed to Italy in 1861. The local museum houses works by Duccio di Buoninsegna, Pietro Lorenzetti, Andrea di Bartolo, Matteo di Giovanni and other Tuscan painters; all taken from local churches. 
The churches of Saints Peter and Paul has a ‘Madonna enthroned with Child’ by Matteo di Giovanni (circa 1450) and a fresco from the early 15th century Sienese school. The fortified ‘pieve’ or Church of Sant’Innocenza a Piana, dates from the 13th – 14th centuries. Most of the little areas surrounding the town have medieval or renaissance castles. The church of St. Lawrence in Bibbiano has a ciborium (a lidded chalice) by Ventura Salimbeni.

Castiglione D’Orcia

Situated in the Val D’Orcia and about 90 kilometres southeast of Florence and 40 from Siena the settlement is first mentioned in 714 and became a free commune in 1252. The following century it lost its independence to the republic of Siena later becoming part of the Grand Duchy of Tuscany and then, in 1861, part of a unified Italy.
Located in the southern part of the province of Siena in an area where Umbria and Lazio meet. Some of the oldest human settlements of central Italy were discovered here at the base of Mount Cetona; the Gosto cave (40 – 80th century BC) and the Lattaia cave (9 – 10th century BC). The Belverde park hosts no less than 25 prehistoric and bronze age caves and there are several Etruscan sites.
The town of Cetona grew on the hillside around the rocca which contains a square tower (circa 900 ad) as well as an inner fortress wall. In the first mention of the comune, at the end of the 11th century, Pope Gregory VII granted feudal rights to a family member which were later sold and, in the 14th century, Cetona was ruled by Siena, Orvieto, Perugia and then Siena again.  An outer wall, containing two towers, was built and then, in 1556, Cosimo de Medici sold Cetona to the marchese Chiappino Vitelli who transformed the fortress into his private residence and also built a piazza, today named Piazza Garibaldi. The word Cetona probably comes from the Latin word Caedita which means felled, deforested; a place that has been cultivated. Archeological finds are on display in the Cetona civic prehistoric museum which also administers the Archeological park. Churches in Cetona are the Chiesa di San Michele Arcangelo (1155), the Collegiata della San Trinita (1475), the convento di San Francesco (1212) and the Convento Maria a Belverde with fresco by Cola Petruccioli of Orvieto.


Chuisi, or Clusium as it was known, was once one of the more powerful Etruscan cities but came under the influence of Rome in the 3rd century BC. In 540 AD it was occupied by the Ostrogoths and it then passed onto the local bishop, Orvieto, Siena and then to the grand Duchy of Tuscany. The lowlands around Chuisi are a treasure trove of Etruscan tombs and the museum in the town is one of the most important repositories for Etruscan remains in Italy.
The Romanesque Duomo of San Secondiano was built over a pre-existing basilica in 560 AD and then renovated in the 13th century. It has a separate bell tower, used for defence in 1585, beneath which is a Roman swim pool that dates from the 1st century.
The so called Labyrinth of Porsenna; a series of tunnels under the town, were built in the 6-5th century and were probably used for draining rain water in both Etruscan and Roman times. According to Pliny the elder, the labyrinth was part of a monument including the sepulchre of King Porsenna.

A medieval and Renaissance hill town and municipality, Montepulciano sits high on a limestone ridge at 605 metres above sea level and is 13 kilometres  East of Pienza, 70 km Southeast of Siena,  124 km Southeast of Florence and 186 km North of Rome. Montepulciano is a major producer of food and drink. Renowned for pork, cheese, pici pasta, lentils, honey but most of all for its wine. According to legend it was established by the Etruscans and recent findings prove that a settlement was already in existence in the 4th-3rd centuries BC. During Roman times it was the seat of a garrison guarding the main roads of the area and after the fall it was developed as a religious centre under the Lombards. In the 12th century it was repeatedly attacked by the republic of Siena and was defended with the assistance of the municipalities of Perugia, Orvieto and, on occasion, Florence. The 14th century was characterised by stuggles between the local noble families until the Del Pecora family became the rulers. From 1390 Montepulciano was a loyal ally (and later possession) of Florence and lived in a period of splendour until the mid 16th century when architects such as Antonio da Sangallo the elder, Jacopo Barozzida Vignola, Baldassarre Peruzzi, Ippolito Scalza and others, built luxurious residences. In 1559, when Siena was conquered by Florence, the importance of Montepulciano declined. After the unification of Italy the town remained an important agricultural centre whilst industrial activities moved to Chuisi which was nearer to the railway line that was being constructed at the time.

Monteroni d’Arbia

The name derives from a combination of the hill top location, Monte Roni, and the river Arbia. Located on the ancient Via Francigena (the old pilgrim route from Canterbury to Rome; once known as Via Cassia) the area was of great agricultural importance to the republic of Siena. Monteroni d'Arbia is set amidst the picture postcard ‘Crete Senesi’ with rolling cultivated hills that are interspersed with vineyards, olive groves and fields of poppies and sunflowers. Stately cypress trees line many roads, and there are castles, villas and farmhouses scattered around the countryside. It is a wonderfully pastoral setting in close proximity to Chianti, the famous wine region of Tuscany, and it is also famous for one of the oldest breeds of cattle in the world; the prized white ‘Chianina’ of the Valdichiana. Also nearby are the well-known towns of Asciano and Buonconvento, not to mention Florence, which is about 80 kilometres to the north.
The most important monument is the medieval fortified mill, imposing and still almost intact, it has a brick built keep and mill pond all of which date back to the first half of the 14th century when it was thought to have produced up to half a ton of flour a day.
A short distance away at Cuna there is the fortified farm; built in 1224 it is a fascinating glimpse into a long gone lifestyle, with walls to protect the families and animals that lived within them. Originally a safe haven for pilgrims and merchants travelling along the road to and from Rome, it eventually underwent changes and in 1314 a fortified granary was built to safeguard the store of grain and other cereals. The pre-existing church was dedicated to Saint James and Christopher, and the remains of 14th century frescoes can be seen there. 
The Pieve or church of St. John the Baptist at Corsano pre-dates 1031; with a nave and two aisles it is Romanesque in style, with both Pisan and Lombard influences. The church contains two late 16th century canvasses by Alessandro Casolani, currently under restoration.
Lucignano d’Arbia is a circular fortified village with 13th century gates and keeps. The 12th century church of John the Baptist houses a crucifixion by Bartolomeo Neroni, nicknamed ‘il Riccio’ presumably because he had curly hair or maybe because his hair was very straight.


Located on the right bank of the Val Di Merse it is situated on the ‘Colline Metallifere’. The castle of Monticiano is forst mentioned in documents dating back 1171 when it was under the rule of the bishop of Volterra. During medieval times the forests represented an extremely important natural resource for the area; not only did they provide the obvious but also several important foods such as wild game and chestnuts. A system of agriculture quickly grew up around Monticiano, the principal product being wheat. In 1266, due to the citizens’ participation in the Ghibelline defeat at Benevento, it was occupied by Sienese troops who destroyed the castle walls. In 1554 Monticiano became part of the Grand Duchy of Tuscany and from 1629 until 1749 it was a fief of the Pannocchieschi family. In 1860 the 723 inhabitants unanimously agreed to join the kingdom of Italy. During the second world war partisans from the Siena area started their first organizational operations in Monticiano, where a resistance brigade, named after Spartaco Lavagnini, also operated. Particularly remembered is the night-time battle between the Germans and the partisans that took place in the main square between the 3rd and 4th of June 1944.

This little medieval village is located in an area of unspoiled nature, with characteristic Tuscan hills and endless vineyards. It is about 20 km to the southwest of Siena and about 70 km south of Florence. Set amongst the valleys of the Merse, Arbia and Ombrone rivers, the municipality has a surface area of approximately 115 square kilometres. The location is convenient as many places of historical and artistic importance can be accessed very easily by car; Siena in 20 minutes, Florence or the coast in less than an hour, Montalcino, Chianti, Pienza, S. Antimo, S. Galgano in 30 minutes and these are only a few examples!
Murlo used to be the capital of the vast region that surrounds it, and once belonged to the diocese of Siena and its bishops. In fact the castle of Murlo, built in 1000 AD, was home to the bishops of Siena for many centuries. The village stands on a hill, protected by stone walls dating back to the 13th century. The area around it is home to many archaeological treasures including castles, farms, settlements and small churches. An ancient Etruscan village was discovered only a few kilometers from Murlo and, amongst the ruins, the archaeologists found an Etruscan temple dating back to the first half of the 6th century BC, one of the earliest places of worship in the area. Interestingly, recent analysis showed that the DNA of the Murlesi (the name given to the inhabitants) is more akin to Etruscan DNA than to that of other Italian samples, probably due to the fact that the area was cut-off from trade, invasions and migrations for many centuries. Today, part of the old settlement has been reconstructed inside the museum of Murlo; a building in the main square that was once the residence of the bishop. The only access into the village is via the old stone gate of Ponente that opens up to the main square, facing the church of San Fortunato.


The "touchstone of Renaissance urbanism" is also in the Val d’Orcia, between the towns of Montepulciano and Montalcino. In 1996, Unesco declared the town a world heritage site and in 2004 the entire valley was included in the list of Unesco’s world cultural landscapes. Pienza was rebuilt from a village called Corsignano, which, in 1405 was the birthplace of Enea Silvio Piccolomini, a Renaissance humanist born into an exiled Sienese family, who later became Pope Pius II. Once he became pope, Piccolomini had the entire village rebuilt as an ideal renaissance town. Intended as a retreat from Rome, it was the first example of humanist urban planning, a concept that was adopted first by other Italian towns and cities and later to other European centres. Though a relatively small town, there is plenty to see in Pienza.
The main square (a trapezium in shape) is defined by four buildings;
- The Palazzo Piccolomini – on three stories with an internal court and a loggia overlooking the formal Italian garden below which there is a vaulted stable.
The Duomo – which dominates the centre of the main square and is one of the earliest designed in the Renaissance manner. The use of pilasters and columns standing on high dados and linked by arches was novel at the time. The bell tower on the other hand has a Germanic flavour as does the internal layout. Pius spent many years in Germany and liked the effect of light in the German churches. Works of art in the Duomo include five altar paintings from the school of Siena by Sano Di Pietro, Matteo di Giovanni, Vecchietta and Giovanni di Paolo.
The Palazzo Vescovile – Home to the Diocesan and Cathedral museum. The construction was financed by Cardinal Rodrigo Borgia, who, at the time the Vatican vice chancellor and later became Pope Alexander VI. The palace was constructed to house any travelling Bishops who came to attend the Pope. Paintings include 14th century works by Pietro Lorenzetti and Bartolo di Fredi as well as a Madonna attributed to Luca Signorelli.
The Palazzo Comunale – When Corsignano was given a city status it required a grand palazzo, something suitably showy. The council chamber is above a three-arched loggia and there is brick bell tower that is lower than its counterpart at the cathedral. For obvious reasons!
The travertine marble well in the square has the Piccolomini crest and was widely copied in Tuscany over in the next 100 years. Other buildings in Pienza - Dating from the same era include the Ammannati Palace, a row of three palaces (Jouffroy, Buonconti and Lolli) which are along the street behind the Bishop’s Palace. Also of note is the church of San Francesco with gabled facade and Gothic portal. It is one of few surviving buildings from the old Corsignano and is itself built on a pre-existing church from the 8th century. The interior contains frescoes depicting the life of Saint Francis; those on the walls were painted by Cristofano di Bindoccio and Meo di Pero, 14th century artists of the Sienese school.
The Romanesque Pieve of Corsignano is also located nearby and the Monastery of Sant Anna in Camprena was founded in 1332/4 by Bernado Tolomei as a hermitage for the Benedictines. The refectory there houses frescoes by guess who? ‘Il Sodoma’ of course! The area of Monticchiello is home to a Romitorio, a series of grottos that were carved into the rock by hermit monks. The church of Saints Leonardo and Christoper is In the same area and was re-built in the Gothic style in 13th century.


Located in the natural park of Valdorcia about 110 kilometres southeast of Florence and 60 Southeast of Siena, the main landmark of Radicofani is the castle or ‘rocca’ which has been documented as such since 978. It is of Carolingan origin and occupies the highest point of a 896 metre high hill. It was restored in the 1560’s and has two lines of walls; the external one being of a pentagonal shape whilst the inner one is triangular with a ruined tower at each corner. Also of note is the Romanesque church of San Pietro which houses works by Andrea della Robbia, Benedetto Buglioni and a relative with the same surname, Santi. Also by della Robbia is the Madonna with saints on the altar of the church of Sant’Agata.


Montalcino is a hill town and municipality famous for its Brunello di Montalcino wine. The town is located to the west of Pienza close to the Crete Senesi in the Val d’Orcia. It is 42 kilmetres from Siena, 110 from Florence and 150 from Pisa and Monte Amiata is close by.
The hill upon which it sits has probably been settled since Etruscan times and it was first mentioned in historical documents in 814 AD. The documentation suggests that there was church there in the 9th century, probably built by monks associated with the nearby abbey of Sant’Antimo. In the middle of the 10th century the population suddenly increased when the fleeing inhabitants of the nearby town of Rosella took up residence. The name of the town comes from a type of oak tree that once covered the area. The view from the town is stunning and looks out over a landscape dotted with silvery olive groves, vineyards, fields and little villages. The lower slopes of the hill are, of course, dominated by highly productive vineyards. In medieval times the city was known for the production of high quality leather goods but, as time passed, Montalcino, like many medieval hill top towns, went into decline  though it did enjoy long periods of peace and prosperity punctuated with a number of extremely violent episodes.
During the middles ages Montalcino had considerable importance due to its location on the Via Francigena but it increasingly came under the thumb of the larger and more aggressive city of Siena. As a result of this Montalcino became deeply involved and affected by the conflicts, particularly in those involving Florence in the 14th and 15th centuries. Once Florence and the Medici family conquered Siena in 1555, Montalcino held out for almost four years, and it remained under the control of the Grand Duchy of Tuscany until the unification of Italy in 1861.    

San Casciano dei Bagni

Covering and area of 91.8 square kilometres the municipality of San Casciano dei Bagni is about 110 kilometres southeast of Florence and about 70 kilometres southeast of Siena. It is deemed to be one of the ‘Borghi piu belli d’Italia’. The history of the area is connected to the presence of hot springs of which there are 42 with a mean temperature of 42° and a daily delivery of 5.5 million litres! According to legend the ‘Balnea Clusinae’ were founded by Porsenna, an Etruscan king of Chiusi. The baths were also very popular during Roman times with Augustus being one of the users. In renaissance times the baths attracted visitors from all over Europe but the 19th century saw a decline that began to recover only in the early 21st century. 

San Giovanni d’Asso

San Giovanni d’Asso is about 80km southeast of Florence and 30km from Siena; again in the area known as the ‘Crete Senesi’. The town takes its name from the parish church, dedicated to St John the Baptist, and the Asso stream, which originates in Orcia. The origins of the San Giovanni d’Asso are ancient; recently there were remains of an ancient 5-6th century church found along the road that connects the town with Lucignano d’Asso. The hamlet is overlooked by a large castle which is home to the white truffle museum, and there is a festival celebrating this rare and fragrant tuber every year. Also interesting are the churches of San Giovanni Battista and San Pietro in Villore, both of which have medieval origins.

San Quirico d’Orcia

Lying within the stunning Crete Senesi in the Val d’Orcia, San Quirico is located about 80 km southeast of Florence and 35 km southeast of Siena. Located on the Via Francigena on the road between Montalcino and Pienza, visitors often overlook its walled charm in favour of its more famous neighbours, but the road to it is one of the most famous and outright beautiful stretches of road in all of Italy. The town was named in honour of Saint Quiricus, a 4th century child martyr.
The area of the municipality known as Vignoni houses a castle that was once the residence of the Salimbeni brothers, artists in the 12th century. It includes an open tower and the Romanesque church of San Biagio  which once housed a crucifix (now in the museum of Montalcino) by one of the most important court sculptors of the Medici court, Giovanni da Bologna. There is also the re-built 15th century palazzo degli Amerighi where plotting took place against the Spanish who menaced Siena in 1558 – 1559. San Quirico has other churches including the collegiate church of San Quirico which dates back to the 8th century (the current structure is a more ‘recent’ 12th century construction), the church of San Giovanni Battista at Bagno Vignoni and the Church of Madonna di Viteleta which has a ceramic Madonna attributed to Andrea della Robbia.


Sarteano is between the Val D’Orcia and Valdichiana about 100 kilometres southeast of Florence and 60 from Siena. The area has been inhabited for thousands of years and is therefore rich from an archaeological point of view, many of the objects found form part of the collection that is in the Civic Museum and some of the most important Etruscan tombs in Tuscany are located in the countryside surrounding Sarteano. 


Sinelunga was, from the 12th century up until 1864, known as Asinalunga. It was here that the Sienese defeated the English mercenaries of Niccolo da Montefeltro in 1363 and where, in 1867, Vittorio Emanuele II arrested Garibaldi in order to prevent an ill-timed descent on Rome. The 16th century collegiata of San Martino was built over an already existing castle in 1588 and was restored in 2010. Inside are works by Benvenuto di Giovanni, ‘il Sodoma’ and Rutilio Manetti.
Things to see; The Palazzo Pretorio, built between 1337 and 1346. The Church of Santa Lucia (1278) which is now an auditorium. The 15th century church of Santa Croce houses the Marriage of the Virgin by Signorelli. The church of San Pietro ad Mensualas was built on a pre-existing Roman building in the 4th century.

The first medieval walls were built in the 13th century and the pentagonal fortress in 1361. The fortress incorporates some of the pre-existing walls and structures including the keep of San Martino, the tower of San Giovannni and the basilica. Though the town was eventually conquered the fortress never was; amazing considering the strength of the Sienese and Florentine forces that besieged Montalcino at various times.

Things to see;
The 13th century church of Sant’Agostino, and adjacent museum, holds two beautiful 15th century wooden sculptures, several in terracotta as well as some 20th century works. The Duomo, dedicated to San Salvatore, was originally built in the 14th century but now has a neo classical appearance thanks to renovation work carried out in the early 19th century. In the charmingly named Piazza della Principessa Margherita, the principal building, with a very tall medieval tower, was built in the late 13th early 14th century. It was once the Palazzo dei Priori but is now the town hall. Close by is La Loggia, a renaissance structure with six round arches which was started at the very end of the 14th century. The 13th century church of san Francesco in the ‘Castlevecchio’ area of the town has undergone restoration over the years, some of the frescoes were done by Vincenzo Tamagni in the early 16th century.
Recently the gradual economic decline of Montalcino has been reversed due to the increasing popularity of the town’s famous wine which is pressed from the locally grown  Sangiovese grapes. The number of wine producers has grown from 11 up to more than 200 since the 60’s and more than 330,00 cases of Brunello are produced per year.
Like many Tuscan and Umbrian medieval towns and cities, Montalcino was divided into areas with their own specific names, colours, songs etc. This tradition still remains and twice a year the inhabitants of Montalcino dress up in authentic costumes and meet together in an archery contest.  In 2010 the Festa Europea della Musica had its first edition and has since been celebrated every year on the 21st of June.

Torrita Di Siena

Is in the Valdichiana approximately 80 kilometres southeast of Florence and 40 Southeast of Siena. The town dates back to the 11th century and at the beginning of the 12th it was ruled by the Republic of Siena. The strategic position meant that the town endured numerous attempts at invasion before becoming part of the Grand Duchy of Tuscany. The town is famous for Ghino di Taco, a 13th century ‘gentleman brigand’ similar to Robin Hood. It is also famous for an annual donkey race.


Trequanda is approximately 70 km southeast of Florence and 30 km southeast of Siena, between the town of Sinalunga and the picturesque village of Montisi. The Municipality contains the villages of Castelmuzio, Petroio and of course Trequanda. Like many towns in Tuscany, Trequanda lies on a hill, surrounded by thick forests and orderly olive groves and vineyards. The most significant monumental buildings are to be found in the old town including the castle of Cacciaconti with an imposing cylindrical tower. With a façade of white and black blocks, the church of Saints Peter and Andrew contains a fresco by ‘il Sodoma’, a fifteenth-century altarpiece by Giovanni di Paolo, and a terracotta attributed to Sansovino. Around the main town, but many distant hills and valleys away, lie the villages of Castelmuzio and Petroio. Castelmuzio is a compact cluster of dwellings whose occupants still live off the abundance of the ancient olive groves producing a limited quantity of high quality oil. Petroio is a small pottery capital with skilled craftsmen and a museum dedicated to terracotta. No one is really sure where the name Trequanda came from; there was an Etruscan hero called Tarkonte after whom the village could have been named, though a more likely solution is that it came from the word  ‘terram quadram’ which apparently means ‘unusual land’. A final option is that it comes from the fact that there are three gates in the city walls ‘treguarda’ (three guards?). None of the solutions are particularly satisfying but the name is lovely!
The first inhabitants were the Etruscans and Trequanda was mentioned for the first time in 1198. Because of its strategic position on the road between Siena and Chiusi it was continuously interfered with by the Republic of Siena and, during the long power struggle between the Guelphs and the Ghibellines, it was used as a base to escape to by the latter. It was later annexed by the grand Duchy of Tuscany. The Gothic–Romanesque parish church was built in 1327 and was later renovated in the Renaissance style. It houses an Ascension attributed to ‘Il Sodoma’ (who certainly got around!) and a terracotta statue of the Madonna with Child that is attributed to Andrea Sansovino. The 15th century high altar is by Giovanni Di Paolo.


Chianciano Terme is between the Valdichiana and the Val D’orcia about 90 kilometres southeast of Florence and about 50 southeast of Siena. It can trace its history back to the 5th century BC, and the Etruscans built a temple dedicated to the god of health close to the Silene springs where the new area of Chianciano (the Terme part) stands today. The curative power of the water became known in Roman times and as a result luxurious villas were built close to the thermal baths. The town’s development was speeded up by the proximity of the Via Franigena and it became autonomous in 1287. In the 14th century the city states of Orvieto and Siena contended for ownership of with Siena eventually being the victor.
Present day Chianciano Terme has two distinct areas; Chianciano Vecchia, located on a hill-top and the Terme area which grew up around the springs. 
The Church of the Immacolata; restored in 15898 after the Florentine conquest of Siena, once housed ‘The Annunciation’ by Niccolò Betti, ‘The Holy Family’ by Galgano Perpignani as well as a fresco of the Madonna of Peace attributed to Signorelli. These works are currently in the museum of the church of San Giovanni Battista which also houses a 16th century fresco of a holy scene, a 14th century crucifix and a wooden dead Christ by Paleari (1783).
Today the Terme section is considered among the finest health resorts in Italy; its therapeutic water is reputed to cleanse the liver by increasing the production and excretion of liver bile! There are also spas for those with respiratory problems and for the treatment of kidney and urinary problems. The Chianciano museum of art has a large collection of contemporary and ancient works.

Areas we cover in the province of Arezzo


Arezzo is an ancient Etruscan town, Arezzo is now a busy place with a pleasant city centre full of shops and restaurants. It has a less touristy feel to it than many Italian cities in Tuscany. The chief draw for visitors is the fresco cycle by Piero della Francesca in the apse of the Franciscan church, San Francesco. Other attractions include the Piazza Grande, a small Piero della Francesca fresco in the Duomo and the house of Giorgio Vasari, painter, architect and the author of “Lives of the Artists”, a who’s who of medieval and Renaissance artists. It was said that Vasari was a good writer, a reasonable architect and a mediocre painter. You can judge the last two for yourself if you look at the Loggia di Vasari in the Piazza Grande and then visit his house which is covered in his paintings. Arezzo also hosts perhaps the largest antiques market in Italy on the first weekend of every month.

The church of San Francesco is home to a superb fresco cycle depicting The Story of the True Cross by Piero della Francesca. The story is very convoluted and it is made harder to follow because Piero della Francesca has depicted parts of the story with parallel themes opposite each other (e.g. two battle scenes face each other across the apse). Visually it’s very pleasing, but it doesn’t help with the order of the narrative. The best way to appreciate the story is to read about it beforehand and then ask for the guide-sheet when you go in. The paintings are breathtaking but are also very popular. At the far end of the Duomo on the left hand wall you can find another Piero della Francesca fresco depicting Mary Magdalene, the lights come on for about 30 seconds when you approach it.
Piazza Grande is the main square in Arezzo, the piazza has the arches of the Loggia di Vasari running along one side and the back of the Pieve di Santa Maria, a church with an impressive campanile (bell tower). Even if you agree with the description of him as a mediocre painter, the extensive frescoes covering Vasari’s house from top to bottom definitely make it worth a visit.


Cortona is the Tuscan hill town with a very long history, made internationally famous in the 21st century by Francis Mayes in her book “Under the Tuscan Sun”. Cortona, very close to the Tuscany-Umbria border, is surrounded by Etruscan walls, around 3000 years old, and retains much of its history through its architecture, layers of history built upon the Etruscan core. There are stately buildings in lovely soft sandstone, hidden Etruscan and Roman wells, interesting medieval architecture and beautiful views over the Val di Chiana.
Cortona is a lively place to spend your time - great art, great atmosphere, stupendous views to Lake Trasimeno and beyond. It is also famed for its art and antiques market in a magnificent natural setting, and various musical and artistic events. The annual crossbow competition in June, the ‘Giostra dell’Archidado’, first played in 1397 is well worth a trip. Visit the Church of the Madonna del Calcinaio painted by Francesco di Giorgio Martini, (1485-1513), and then go up to the Piazza della Repubblica to see the Palazzo Comunale and Palazzo Casali (housing the Museo dell'Accademia Etrusca, and the Museo Diocesano (with works by Luca Signorelli, Beato Angelico, Sassetta, Lorenzetti, etc.). Many travellers come for a day trip and end up spending several more days...

Castiglion Fiorentino

Castiglion Fiorentino is a small, walled city in eastern Tuscany, between the cities of Arezzo and Cortona. The town has a colourful history, having changed hands and names many times during the various wars of the 14th-17th centuries. Among historical sites to take in are the fortress of Cassero, completed in 1367, and the Romanesque church of Sant’Angelo, completed in 1239 and built on the site an an ancient Etruscan temple. It is well known for its annual festivals, including the local version of Siena’s Palio, entitled the ‘Palio dei Rioni’ and entailing a hair raising gallop around Piazza Garibaldi.

Foiano della Chiana

Foiano della Chiana is a small agricultural town in eastern Tuscany, between the cities of Sinalunga and Cortona. According to a legend, the name derives from the god Janus who, when he went up the Tiber River and settled in the shadow of a hill, called it Flos Janus. A parchment dating back to 842 AD was found in which Lothar I mentions the Roman Campus Fugianus. It is well known for its annual carnival, Italy’s oldest dating from 1539. The town’s four districts, or cantieri, compete each year for the prize for the best float, which are towering 20ft high papier-mâché figures with moving limbs and heads, stunning in their intricacy and usually frightening for small children! An effigy of Giocondo, King of the Carnival is made from straw and rags, and is burned in the main square as a form of collective purification for the people of Foiano.

Monte San Savino

Another pretty hilltop town, close to Foiano della Chiana on the edge of the Chiana Valley. Monte San Savino is surrounded by sloping walls with four gates: the main one, Porta Fiorentina, Porta Romana, Porta San Giovanni and the so called porticciolo.

Some of the principal monuments are in Piazza Gamurrini. The town museum is in the castle. The steeple built in 1643 in honour of Mattias de Medici towers over the square. In 1652 the Church of Saint Clare was built next to the castle. Inside one can admire a work of art by Sansovino featuring the Virgin with Baby Jesus and Saints, an altarpiece by Sansovino of Saint Laurence, Saint Rocco and Saint Sebastian, a Crib and a statue of Saint Anthony the Abbot. Palazzo Di Monte is on corso Sangallo.


Lucignano is a beautifully conserved medieval village in the Val di Chiana, both walled and on a hill-top it is elliptical in shape and strategically placed between Siena and Arezzo. Lucignano was already surrounded by a wall in in 1371 and was further fortified by the Florentines, upon the wishes of Cosimo de Medici, with the construction of a fortress in around 1558. The concentric roads that circle the village eventually reach the centre that is characterised by the Palazzo Comunale (town hall), the collegiate Church and the Church of St. Francesco.


Anghiari has been nominated one of the most beautiful small towns in Italy and well deserves the title. Perched on the side of a hill it really is picturesque and though you need strong thighs to get around it really is well worth a visit.
The origins of the town are roman but it became much more important during the middle ages because of the strategic location. Anghiari is famous for a battle fought and won by the Florentine Republic against the Milanese army; an outcome that kept the central Italy in the hands of the Florentines. Machiavelli subsequently wrote about it and pointed out that amazingly, despite a full day of skirmishing, only one soldier died and that was because he fell from his horse.
However important the battle was at the time it would almost certainly have been forgotten about if the magistrates of Florence hadn’t decided to decorate the walls of the Palazzo Vecchio with scenes celebrating the victories of the Florentine army. Michelangelo was commissioned to paint the Battle of Cascina and Leanoardo Da Vinci the Battle of Anghiari. Unfortunately, the experimental drying process that Da Vinci was testing was unsuccessful and the incomplete painting was destroyed.
It was eventually replaced by the Vasari and the legend of the lost Leonardo began.
These days local events are a little less aggressive and every year at the end of April beginning of May there is an extensive craft fair within the town walls. There is also an artisans market and the ‘Anghiari festival’ takes place every year with concerts by the Southbank Sinfonia Orchestra from London.


Is a lovely little hill top village most famous for being the home of Piero della Francesca’s Madonna del Parto. Painted between 1455 and 1465 the fresco is in honour of the artist’s mother who was born in Monterchi. Once located in a little church just outside of the village, the fresco now has a little museum all to itself.
The name of the town is said to derive from the latin ‘Mons Herculis’, according to legend  the demi god Hercules is said to have founded Monterchi after having defeated the multi-headed Hydra.
On a tastier and less gory note, Monterchi is also know for a Polenta festival that has been held every September since 1973. 


Sansepolcro, formally Borgo del Santo Sepolcro and often referred to as ‘Borgo’ by the locals, was birth place to a number of famous individuals including Dionisio Roberti, Piero della Francesca, Luca Pacioli, Cherubino Alberti and Matteo di Giovanni. This lovely town is located on the banks of the Tiber in the extreme east of Tuscany, north east of Arezzo. Sansepolcro is a reference point for four regions; Tuscany, Marche, Umbria and Emilia Romagna. 
The town was founded in the 10th century by Arcano and Egidio, two pilgrims who returned from the holy land and set up a monastic community. The town grew up around the abbey which was dedicated to Santo Sepolcro and the four holy evangelists. One of the reasons for the town’s development was the fact that in 1083 Emperor Corrado II allowed the abbot to organise a market on Saturdays and an annual fair at the beginning of September; an annual fair that still exists today.
The town passed through various hands in the passing of the years; from Uguccione della Faggiuola, Guido Tarlati, the city of Perugia, the Visconti of Milan, Città di Castello, the Papal states and the Malatesta family from Rimini! This period, from 1370 onwards, is considered to be the most splendid of the town’s history. After that it became a feudal town and in the XIII and XIV centuries it assumed the characteristic walled look with twenty or so public and private towers including the ‘Torre Di Berta’. After the battle of Anghiari Pope Eugenio IV ceded the town to Florence for the sum of 25,000 ducats.
In the XIV and XV centuries the economy of the town was healthy mainly due to the cultivation of woad; one of the most well used dyes in the fabric industry at the time. In the XV century the town was referred to as Biturgia and today the residents of Sansepolcro are still called Biturgensi.
During the course of the XVI century the town was elevated to city status by Pope Leone X and at this point the city underwent a significant artistic flowering. The proximity of the Umbria, Emilia Romagna and Marche regions facilitated a deep social and cultural rapport in the area which became an economic and cultural meeting place.
In the XVII and XVIII century there was a long period of crisis and a drop in the number of inhabitants due to a serious bout of the plague between 1630 and 1632, that said the preventative measures taken by Bishop Filippo Salvati meant that Sansepolcro didn’t suffer as much as others towns.  
Despite the economic crisis, radical renovation was carried out on nearly all of the churches in the XVIII century and this eliminated nearly all evidence of any medieval architecture. The town suffered earthquakes in 1781 and 1789 and after the latter many of the towers in the town were lowered in height with the exception of the Torre Di Berta which was destroyed by the Germans during the World War 2. Also during WWII the town was saved from destruction by the efforts of Tony Clarke, a British Royal Horse Artillery officer who halted the allied artillery attack in order to save Piero della Francesca's fresco, the Resurrection.
In the 1920’s Sansepolcro underwent a slow phase of social and economic growth mainly due to the birth of the ‘Buitoni’ factory in 1827. The isolation that had held back the development of the town was altered by a train line from Arezzo that passed through Sansepolcro and continued to Città di Castello and Gubbio, as well as the construction of the E45 motorway from Orte to Ravenna in 1959.  
The cultural life of the town was transformed in the 1951 with the Palio della Palestra and the Giochi di Bandiera; ancient cross bow and flag throwing tournaments which have taken place in costume every year since 1951. The civic museum houses many works of art including the Resurrection, deemed by Aldous Huxley to the best painting in the world.
During the war Sansepolcro was home to the Nazi-Fascist Resistance movement and a museum (currently undergoing re-organisation) was established in 1975.
Also worth seeing is the Aboca museum which was established in 2002. Since 1978 the Aboca company has been cultivating and transforming medicinal plants and herbs.

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