Castiglion Fiorentino Tuscany villas
Search +39 346 327 9144 Email

Tuscany Area Guide

You probably already have an idea of just how beautiful this region of Italy is: Rolling hillsides, fields of sunflowers and poppies, vineyards,  fresh food and wine the natural warmth of the Tuscan people. These are just a few of the images you might have thought about when planing your vacation here in Tuscany.

Whilst you are here, we can help organise cooking classes, truffle hunting, car rental, scooter hire and more.

Then there are the Tuscan towns, villages and markets.


Anghiari is well worth visiting all year round thanks to its active cultural life. There are exhibitions, fairs, local festivals, a busy theatre program and an active interest in the conservation and re-enactment of historical and folklore traditions all contributing to the cultural life of the town. Visitors enjoy the enchanting atmosphere enhanced with fairs, markets and open-air shows and the excellent local cooking and warmth of the Anghiarese add their special taste to this superb landscape.

Anghiari is a lovely medieval town lying between two rivers, the Tiber and the Arno. The powerful thirteenth century walls made the town an invincible fortress which constituted an important reference point and kept the Tuscan flag flying during the many historical events that occurred in this delicately balanced border area. On the 29th June 1440 the intra Tevere et Arno to the whole of Europe.

Surrounded by castles and country churches Anghiari looks out over the beautiful High Tiber Valley landscape, a natural amphitheatre filled with the spirituality of St. Francis of Assisi. The countryside around Anghiari has an untouched atmosphere with ancient woods dotted with monasteries and archaeological sites. Artisan shops and the workrooms of furniture and antiques restorers enrich the small squares of the town; its towers and churches are embellished with masterpieces of painting and sculpture and there are breathtaking views and vistas to be found from every corner of the ancient town.


Capital city of the Tuscan province, Arezzo perches on a hill, south and east of Florence, overlooking the Arno and Tiber River valleys. This geographical position has favoured the development of artisans (especially gold craft) and industrial activities. The city has given birth to famous people like Petrarch, Aretino and Vasari, and has maintained an extremely interesting historical and artistic tradition since the Middle Ages. The historic centre contains stupendous works of art and testimonies from every era.

Arezzo has a monthly antique market held on the first weekend of each month when hundreds of stallholders come from all over Italy and visitors crowd the streets of the ancient city centre.

One of the many famous churches in Arezzo is the Church of S. Francesco , which is a 13th century Gothic construction. The church contains paintings by important artists such as Loretino d'Arezzo, Spinello Aretino, Niccolò di Pietro Aretino, and Piero della Francesca, some of whose most important works are in this church. Restoration of his Battle between Hercules and Cacus and the Discovery and Proof of the True Cross by the Superintendence of Arezzo and the Opificio delle Pietre Dure of Florence, which started in 1985, has recently been completed and the public can now view them


The medieval village of Trequanda is crowned by the remnants of the ancient Cacciaconti castle. There is also the parish church of the Saints Peter and Andrea, dating back to the 13th century. It is a beautiful Romanesque-gothic construction with a particular facade covered with white and ochre colour stones forming a geometrical chessboard pattern. 

San Gimignano

San Gimignano  - The original Manhattan!

Think of Cher, Maggie Smith and others in the film: Tea with Mussolini...

From every angle San Gimignano’s appearance is medieval. Perched on a hill with its towers and green mountains behind it offers one of the best views of the Tuscan countryside. 

Of the 72 towers that once defined the profile of San Gimignano, only 14 remain. (The film “ Tea with Mussolini”, taken from Franco Zeffirelli’s autobiography, suggests that a group of English and American women saved the remaining towers towards the end of the Second World War) 
Around the Piazza del Duomo are a number of its monuments, including palaces, the cathedral with its famous frescoes, and 7 of the 14 remaining towers. The triangular Piazza della Cisterna, which is paved with stones set on edge, has a well in the centre. These squares date to the 13th and 14th centuries

In addition to the churches and other buildings, another attraction of San Gimignano worth a visit is the Museum of Torture - featuring such ancient relics as a fingernail clamp and a metal pig's head which, some say, medieval women were temporarily forced to wear for nagging their husbands too much!
Wine: Vernaccia di San Gimignano, made from the grape of the same name, is one of the best-known wines in Italy and the world. There are many vineyards in the area where tourists are welcome

Driving distances:

Castiglion Fiorentino to San Gimignano – 62 miles / 100 kilometers


Palio, Piazza del Campo, Gothic Architecture...

Siena has retained much of its medieval architecture and charm, including walls and gates that surround the city.  The cathedral (11th-14th century) is one of the finest examples of Gothic architecture in Italy and some say it is the most stunning cathedral in Tuscany. Here you will find works of famous Renaissance artists including Michelangelo, Pisano, Donatello and Bernini. Another interesting feature is the marble mosaic floor dating from 1369
The Gothic-style municipal palace, begun in 1288 and finished in 1309, now houses the city archives, including certificates and documents designed and executed by famous Sienese artists.

The famous Piazza del Campo, where the famous Palio horse racing takes place, with its stunningly beautiful Town Hall, is a spectacular example of Renaissance art and architecture. 

Siena's intimate medieval streets are lined with both local handicraft shops and some international chains.

San Giovanni d'asso

San Giovanni d'asso  has a castle, which in November hosts the famous White Truffle Market.

The ancient Romanesque church of San Giovanni Battista is close to the castle, while in the lower part of the village lies the most important church in the area San Pietro in Villore. 

Within the locality is the picturesque village of Montisi, with its Chiesa dell'Annunziata and its historical grain tower. Here, every year, on the Sunday nearest to the 5th of August (the Festival of the Madonna delle Nevi and a jousting contest - the "Giostra di Simone" - takes place.

The drive from here to Montalcino and Pienza, is one of the best dives in Tuscany....


Montalcino is completely surrounded by ancient walls and some of the original 19 towers can still be seen, as well as some of the fountains. The impressive fortress, built in the second half of the 16th century is still intact and from its ramparts there are magnificent views across the Val d'Orcia. The surrounding countryside is now devoted to the production of the wine acclaimed throughout the world - the Brunello, and the younger Rosso di Montalcino. Friday is market day.

The Abbey of Sant'Antimo, which is about ten minutes from Montalcino is also well worth a visit. You may be lucky and hear the monks chanting.


Torneo di Apertura della Cacce (Tournament for the Opening of the Hunting Season) - Second Sunday in August. This festival marks the beginning of hunting season. The festival starts with trumpeters and drummers. In the afternoon, a costumed procession proceeds to the fortress where archers from the four neighbourhoods (Borghetto, Pianello, Ruga, and Travaglio) compete in an archery tournament. 

Sagra del Tordo (Festival of the Thrush) - Last Sunday of October: The festival kicks off with a town crier who walks through the streets announcing the start of the festival to the accompaniment of drums. A dance called the Trescone is performed in the streets. Later a procession to the fortress takes pace with residents in 14th century costumes, rolling flags, trumpets and drums. This marks the beginning of the food fair, which includes typical local dishes such as polenta, pinci, bruschetta etc, as well as Brunello and Roso di Montalcino. At the fortress, the four neighbourhoods (Borghetto, Pianello, Ruga, and Travaglio) compete in an archery tournament and a torchlight procession marks the end of the festivities.


Michaelangelo, Canaletto, da Vinci, Botticelli, Raffaello etc.

Florence should definitely be on your itinerary. Full of history and well-known attractions - appealing for travelers of all ages. (an hour from Castiglion by train) 

A distinctive feature of Florence's skyline is the Duomo, Santa Maria del Fiore work on which started in 1296, and the Campanile (bell tower). Opposite the cathedral stands the Baptistery dating from 11th century. The Florentines commissioned a series of bronze doors with relief sculptures. The third pair of these doors, by Lorenzo Ghiberti, were of such rare beauty that Michelangelo christened them the  ' Gates of Paradise.'
There are many galleries and museums in Florence; the most famous is Galleria dell'Accademia as it contains one of the most famous statues in the world, Michelangelo's David. Michelangelo's David originally stood in front of the Palazzo Vecchio at the beginning of the sixteenth century but in 1873 it was moved to the Galleria and was replaced by the copy, which now stands in its original location.

The De Medici family founded the Uffizi Gallery in Florence in 1581. It is one of the oldest museums in the world. Many important works of Italian and other schools, dating from between the fourteenth and eighteenth centuries are on view here, including the largest collection of Tuscan Renaissance paintings. The gallery features works by Botticelli, Canaletto Michelangelo, Raffaello, and da Vinci - to name but a few.

The Ponte Vecchio (old bridge) is unique because it is the oldest surviving bridge in Florence. Originally, It was used by blacksmiths, butchers, tanners and others who used the river as sewer. Towards the end of the Renaissance period, goldsmiths and other artisans established themselves there. Ponte Vecchio is the only bridge in Florence that survived W.W.II.

There are many shops and markets in Florence some more famous than others. One worth a visit is Farmacia di Santa Maria Novella. The pharmacy dates back to the 17th century and is open to the public in its original form. When you go into the shop the aroma of the preparations, and the sight of this monumental environment immediately overwhelm you.

There are many other attractions both in the city and on the outskirts. These include gardens and villa, and just outside Florence is Fiesole – well worth a visit 

Castiglion Fiorentino

This historic Tuscan Town lies at the center of a triangle formed by important cities such as Florence, Siena and Perugia. 

Castiglion Fiorentino, originally an Etruscan settlement and later an old medieval village, lies close to the famous Valdichiana and Cortona.

The tower of the ancient castle dominates the town. This charismatic town has much to offer any visitor including its beautiful medieval walls, beautiful churches, art treasures and numerous Renaissance structures - e.g. the Loggia by Vasari at the Piazza del Municipio.

The first of the existing city walls, including Porta Fiorentina, the main entrance to the town's historical center, was erected in the 13th century, then enlarged in the 14th under the Perugians to connect the castle to the outside walls. An anti-gate containing the Medici coat of arms is located outside of the walls, while the inside of the gate is constructed of three arches under a statue of the town's patron saint, St. Michael. The town's fortress, the Cassero, was completed in 1367. In the 15th century, the nuns of San Girolamo used the fortress as a convent, and by the 19th century much of the fortress had been destroyed, with the remaining structure used as a prison

The Pinacoteca, or Municipal Art Gallery, occupies the former church of Sant'Angelo. Built on the site of an Etruscan temple, the church of Sant'Angelo was built in Romanesque   style between 1229 and 1239. The church has served as a hospital, wine cellar, and workshop before being renovated and used as an official museum and art gallery

Castiglion also has many festivals throughout the year including the famous "Palio dei Rioni" on the third Sunday of June. A smaller version of the similar festival in Siena, the Palio dei Rioni is a horse race around Piazza Garibaldi, including a colorful display of the ancient custom of flag-waving, which dates back to the 13th century. 

In addition to the spring poppies, summer sunflowers and the famous Tuscan Cypress and Olive trees the beautiful green hillsides and country lanes are a must for any traveler any time of the year.


Cortona is now famous for “Under the Tuscan Sun” by Francis Mayes – and late 2002 and early 2003, Cortona was transformed and given the Hollywood once over during the making of the film version – which included a huge set of fountains with Roman lions etc – however, don’t go searching for this as it was merely something installed to make the town “more authentic”!

Cortona with its Etruscan origins is rich in art and history. The prevailing character of Cortona’s architecture is medieval with steep narrow streets situated on a hillside (altitude 600 metres) providing magnificent panoramas to every point of the compass, embracing the whole of the Valdichiana.

The Museo Diocesano is home to a superb collection of paintings, including "Annunciation" and "Madonna and Saints" by Fra Angelico, and also a group of work by Giuseppe Maria Crespi known as Lo Spagnuolo   called "Ecstasy of St. Margaret".

Inside the Palazzo Pretorio is the Museo dell'Accademia Etrusca that displays items from Etruscan, Roman, and Egyptian civilizations and also art and artefacts from the Medieval and Renaissance eras.

Cortona has a range of restaurants catering for all tastes.

As with most Tuscan towns the churches are magnificent and well worth a visit.


Pienza is a small town close to Montepulciano and Siena.

It is a rare example of Renaissance town building. Defined, from time to time as the "ideal city", or the "utopian city", it represents one of the best-planned Renaissance towns. It was here that Renaissance town-planning concepts were first put into practice after Pope Pius II decided, in 1459, to transform the look of his birthplace and gave it its name Pienza ("Pio's Town").

The Duomo  is flooded with light from the vast stained glass windows stipulated by Pius II as he wanted to create a domus vitrea ("a house of glass"). The palazzo Piccolomini is next to the Duomo. It was home to Pius II's descendants until 1968. The apartments, which are open to the public, include Pius II's bedroom and library. At the rear of the palazzo there is an ornate arcaded courtyard with hanging baskets and a triple-tiered loggia. From here there are stunning views across to the wooded slopes of the Monte Amiata. Pieve di Corsignano is where Pope Pius II was baptized. This is an 11th century Romanesque parish church on the outskirts of Pienza. The interior can be seen by appointment via the Pienza Tourist Office (+39 0578 749071)

Pienza was used as the setting for many films including Gladiator and Zeffirelli’s film Romeo and Juliet.


The biggest and highest of southern Tuscany's hill towns Montepulciano has been called the "Pearl of the 1500s" thanks to the numerous works created by famous Renaissance artists.

The main square "Piazza Grande" is surrounded by magnificent buildings such as the Palazzo Pubblico, the Cathedral and several residences by Vignola, Sangallo and Peruzzi. Artistic treasures abound in the many churches. The most beautiful is the tempie of San Biagio.

Montepulciano celebrates several traditional events. Between July and August, Piazza Grande becomes a stage for concerts and for the Cantiere Internazionale d'Arte (International Arts Workshop). At the end of August the people of Montepulciano perform - the 'Bravio delle Botti', a competition between the 'contrade', the different districts of the town, where empty wine barrels are rolled up through the town in a race to Piazza Grande.

And wine is, in fact, the most famous product of the land around Montepulciano. Most of the wine cellars dug into the ground under the town are of historical interest; here visitors may take a break between one museum and another. In the 17th century, when Francesco Redi wrote his poem, Bacchus in Tuscany, he described the Noble Wine of Montepulciano as "The King of all wines.” Around the area are numerous vineyards where you can taste and buy wine.


Assisi is known as the city of Peace. Its main characteristic is its medieval structure that has remained intact over the centuries. The town sits on the slopes of Mount Subasio along overlapping natural terraces. Outstanding architecture, convenient geographical position as well as its mild and dry climate make it an ideal tourist spot all year long.

But of course, Assisi is famous all over the world, thanks to its favorite son, St. Francis. The Basilica of St. Francis houses the tomb of St. Francis and has been a popular pilgrimage destination and tourist attraction. Following the devastating earthquakes of September 1998, the basilica has been fully restored. One of the artistic highlights of the basilica are the frescoes by Giotto and other leading artists of the day. The church has three parts: Upper basilica, lower basilica and the saint’s tomb.

However, Assisi is more than just the home of St Francis. A stroll through the main square, Piazza del Comune, gives an idea of this central Italian town’s rich history. You will find the Roman temple of Minerva, the Roman Forum and a Romanesque tower.

Eremo Le Celle

The famous Le Celle monastery in its beautiful surroundings behind Cortona is visited year round as the place St. Francis of Assisi lived in the 12th Century, before returning to Assisi where he died. This is thought to be the oldest monastery in the world.

Le Celle is a stunning example of a Franciscan convent set on the slopes of Monte S. Egidio, about 3 1/2 km from Cortona.  Saint Francis had it built in the early 1200's. Today one can still see the cell where Saint Francis stayed. 
It is the object of many tourist visits. A lot of people come to pay tribute to St Francis' cell: a narrow quadrangular room, 1.80 x 2.50 m. and only 1.90 m. high. The Saint's bed is still preserved inside, as well as an old sandglass and a copy of a painting of the Madonna and Child in front of which St. Francis used to pray. Through a small window in the wall facing the Torrent one can see the place where the cell of Beato Guido was built, which was destroyed by a serious flood. 

In April, 1226, during an interval of improvement, Francis was moved to Cortona, and it is believed to have been while resting at the hermitage of the Celle there, that the saint dictated his testament, which he describes as a "reminder, a warning, and an exhortation"

Driving Distances:

From Castiglion Fiorentino - 7 miles / 11


Set in the green foothills of Mount Ingino, with spectacular views of the Umbrian Valley, is the ancient town of Gubbio. It is one of the most picturesque and characteristic towns, not only in Umbria but also in Italy, thanks to its nearly intact medieval features. Gubbio has a simple street plan of five parallel streets running at different levels on the slopes of the hill with interconnecting alleyways. 

The buildings are mainly Romanesque in shape. An unusual aspect of the town is the so-called “Door of the Dead”, a narrow pointed arch door above street level, which, according to tradition, was reserved for the passage of coffins. However, a more likely scenario is that they were used as a means of entry to their homes by way of a retractable wooden ladder thus protecting themselves during the middle ages. 

The main building is the Palazzo dei Consoli, which dominates the town.  There is also a Roman theatre - one of the largest surviving of its kind dating from the 1st. century A.D Besides the famous Basilica of St Ubald, there are numerous churches and museums which are well worth a visit along with various shops specialising in local art and craft. A market is held every Tuesday.

This age-old traditional event, which may well date to the pagan era, is normally held the day before the feast day of St. Ubald (16th May), patron saint of Gubbio. The Ceri are three enormous wooden statues of St. Ubald, St. George and St. Anthony. The townspeople carry statues on their shoulders as they race through the historic city centre, up to the Basilica of St. Ubald on the top of Mount Ingino. The high point of the event is the race: as the Ceraioli dash through the city streets and up the steep slope, they are accompanied by the thrilled crowd of shouting onlookers. This one-day event is one of Italy's most traditional and well-known popular/religious events. 

Driving Distances: 

Castiglion Fiorentino / Gubbio – 45 miles / 72 kilometers

Contact Us

For further assistance choosing a villa for your holiday in Tuscany, either send us an email, phone, or use the form on our contact page.


Telephone #1: +39 346 327 9144

Telehone #2 (solo SMS Italiano): +39 333 6406494

Follow Us Online

SecurityMetrics Credit Card Safe

© 2021  Tuscan Charm Ltd. Registered Office: The Apex, 2 Sheriffs Orchard, Coventry, CV1 3PP, UK

To Top