Guide to Points of Interest

Arezzo

Arezzo is the city closest to Poggio del Drago: capital of the homonymous province, it offers a vast amount of artistic, historical, and cultural treasures. The birthplace of illustrious figures such as Francesco Petrarca and Piero della Francesca, in Arezzo you will discover monumental palaces, museums with ancient and medieval artifacts, wonderful churches, and cathedrals – for example, the Basilica of San Francesco or the Cathedral of San Donato – inside which you can admire very important and priceless works of art such as “The Legend of the True Cross” by Piero della Francesca and “The Ark of San Donato” attributed to the Aretine Giovanni di Francesco.

An ancient city, once part of the Etruscan Dodecapolis and over the millennia, became an important cultural, artistic, and economic center, building a historical heritage of invaluable value that is definitely worth an in-depth visit.

Cortona

Cortona is also an ancient Etruscan city that was once part of the Dodecapolis. The city, which has survived millennia, is today a wonderfully picturesque village that will transport you into a late medieval and Renaissance setting with a unique scenario.

In the city, you will find a very interesting museum of Etruscan and Roman art and artifacts, the Renaissance church dedicated to St. Francis of Assisi – which contains relics of the Saint -, the unmissable Diocesan Museum – inside which you can admire the wonderful “Annunciation” by Beato Angelico – and last but not least the Basilica of Santa Margherita, patron saint of the city.

Castiglion Fiorentino

Castiglion Fiorentino is located in an area that we know for certain has been inhabited since prehistoric times, in the Iron Age during the Villanovian Culture period. At the time of the Dodecapolis, Castiglion Fiorentino served as a very important crossroads between the two Lucumonies of Arezzo and Cortona, and since then the village has only grown in splendor, becoming the town that we can admire today in our tour of the Tuscan wonders. Among the attractions of the city, we point out the works of Bartolomeo della Gatta – an illustrious painter born in Castiglion Fiorentino -, first of all “The Stigmata of St. Francis” preserved in the Municipal Art Gallery or “The Lamentation over the Dead Christ” by Luca Signorelli. The architecture of the entire town will fascinate you with its medieval atmosphere: a stop not to be missed.

Anghiari

Anghiari was founded in the 7th century with a Lombard castle, probably built from the structure of an older Roman farm. This, after several changes of ownership, eventually became, in 1104, the property of the Benedictine Camaldolese monks who founded the Abbey of San Bartolomeo Apostolo here, around which the city settlement finally grew.

In Anghiari, the famous eponymous battle was fought on June 29, 1440, later designed by Leonardo da Vinci himself, and over the centuries numerous buildings of great artistic or historical relevance were built, including the Chapel of Mercy or the Marzocco Palace.

The city, already awarded the Orange Flag, named City of Good Living and One of the Most Beautiful Villages in Italy, was included by CNN among the Most Beautiful Villages in Europe in 2022.

Caprese Michelangelo

In this small village of just 1,300 inhabitants, the renowned and illustrious Michelangelo Buonarroti was born on March 6, 1475. The town has carried his name since 1913. In the city, it is mandatory to visit the Michelangelo Buonarroti Birthplace Museum and the Michelangiolesca Library.

Chianti

The Chianti Valley has always been considered the heart of Tuscany. It is the portion of territory between Florence and Siena, Arezzo, and the Pisan Hills: rich in wonderful villages, the region is famous mainly for its wine culture, being the area of origin of the homonymous precious red wine.

Gaiole in Chianti

The small village of Gaiole in Chianti was founded in the 10th century and hosts some characteristic religious, military, and civil architectures, including the Castello di Ama, the Church of San Sigismondo, and Villa Vistarenni.

Castellina in Chianti

Castellina in Chianti is located in an area inhabited at least since the 7th-6th century BC. In the area, we find the Montecalvario mound, an Etruscan tomb near the settlement, and the Poggino Necropolis, near Fonterutoli. The history of Castellina in Chianti is not limited to the Etruscan period, and in the small village, you can admire religious, civil, and military architectural works dating from the 10th to the 18th century.

Greve in Chianti

Greve in Chianti is another medieval village that characterizes the Chianti territory: its history is linked to that of its main square, the venue for important markets since its origins. In the surroundings, we find the castles of Uzzano, Canonica, Mugnana, and Verrazzano, as well as the village of Montefioralle and S. Lucia a Barbiano – with its castle protagonist of clashes between Siena and Florence.

Siena

Siena is one of the most famous Tuscan cities in the world. We could write thousands of words about the historical, artistic, and cultural beauties of the city, and we would still have to make a selection: we will therefore mention only some of the attractions and wonders that can be admired in Siena, first of all Piazza del Campo, dominated by the 88 meters of the Torre del Mangia, which is at the center of a charming itinerary. Do not miss the Siena Cathedral, the Basilica of San Domenico, the castles and the Historic Gates, which refer us to the famous Palio di Siena, a truly characteristic event and worth attending to enjoy the enthusiasm of the entire city.

Monteriggioni

“But as the round of the circle

Monteriggion crowns itself with towers,

so the bank that surrounds the well

towered half of the person

the horrible giants, whom Jove

threatens from heaven still when it thunders”

So Dante Alighieri, in Canto XXXI of Hell, refers to the walls of Monteriggioni, a wonderful fortified village wanted by the Republic of Siena and built in the 1210s. Walking inside Monteriggioni, walking along the evocative walk along the walls or walking outside along the natural paths of the Tourist Park on the Via Francigena offers the thrill of reliving glimpses of the Tuscan Middle Ages and Renaissance: arrived in the Sienese area, the village is a must-see stop.

San Gimignano

Even for San Gimignano Words are not enough to describe the magical atmosphere that this charming village offers to visitors. Its fourteen towers create a spectacular skyline, surrounded by the most beautiful and picturesque Tuscan countryside. The Etruscan Necropolis is also worth mentioning, testifying to the ancient history of the San Gimignano area.

Volterra

Volterra was one of the main city-states of the ancient Etruscan civilization, and during the Renaissance era, it was recognized as a Signoria. Today, it is a walled town with an embarrassment of choices for visitors, including monumental palaces, churches, museums, or just the characteristic streets of this ancient village, a treasure of Tuscany.

Val d’Orcia

Val d’Orcia is a territory so beautiful and with such a marvelous nature that it leaves visitors ecstatic. No wonder this valley with its spectacular atmosphere was chosen by director Ridley Scott to represent the Elysian Fields, the Roman Paradise, in the final scene of the famous movie “Gladiator”.

Pienza

Pienza is a small village located in Val D’Orcia: since 1996, its historic center has been declared a UNESCO World Heritage Site. Pienza is one of the most successful examples of Renaissance rational urban planning. The Cathedral, the Town Hall, the Borgia Palace, and the Piccolomini Palace are some of the monumental structures that you can admire in the wonderful village of Pienza, immersed in the beautiful Tuscan countryside.

Montepulciano

The history of Montepulciano is very ancient: according to legend, it was founded by Porsenna, the Lucumone of Chiusi, and certainly some documents attest to its existence as early as the 4th-3rd century BC. The village overlooks the Val di Chiana and is a place rich in history, with its historic center with a particular S-shaped form full of monumental palaces and surrounded by a unique countryside.

Montalcino

The first thing that comes to mind when talking about Montalcino, the largest municipality in the province of Siena, is its famous Brunello, a high-quality red wine. However, Montalcino does not limit itself to offering visitors the opportunity to taste one of the best wines in the world: surrounded by the Tuscan countryside and rich in historic palaces and monuments – the Fortress, the Town Hall, the Church of Sant’Agostino are just some examples – Montalcino will be a stop that you will not forget on your visit to Tuscany.

Bagno Vignoni

Bagno Vignoni, in the province of Siena, is home to one of the oldest thermal sites. Its Piazza delle Sorgenti contains a hot and steamy water source that originates in the volcanic subsoil. The thermal baths of Bagno Vignoni have been known since Etruscan times, and over the centuries illustrious figures such as Caterina and Lorenzo de’ Medici have chosen the village as a holiday destination.

San Quirico d’Orcia

San Quirico d’Orcia is another municipality in the province of Siena, an ancient village that according to the Dutch Etruscologist Van Der Meer should be identified with Ena, a location mentioned in the Liber Linteus Zagabriensis, the oldest book in Western Europe and the only book in linen in the world. The village is rich in historical, religious, military, and civilian architectures, and it was chosen by Ridley Scott for some scenes of his famous “Gladiator”.

Florence

“Rejoice, Florence, since you are so great, that you beat your wings over land and sea, and through Hell your name is spread!” Dante Alighieri, Inferno XXVI

Florence needs little introduction: certainly one of the most famous cities in the world, in Florence, one is surrounded by artistic treasures at every turn, and its timeless charm attracts millions of tourists every year.

“Lucca

Lucca is a city with a wonderfully preserved historic center: surrounded by its walls, the center houses monumental palaces and many wonderful towers. The city of Lucca is ancient, and archaeological findings date back to the 4th century BC.

Pisa

Pisa definitely dates back to the Etruscan era: its necropolis can be dated back to the 7th-4th century BC, making it one of the oldest Tuscan cities. How can we not mention its famous Leaning Tower or the Piazza dei Miracoli, world-famous attractions that attract millions of tourists every year. Pisa, however, has much more to offer. In its millenary history, the city has experienced periods of greatness and has been one of the famous Maritime Republics ruling the Mediterranean. A beautiful city that definitely deserves a stop on a tour of Tuscany.