What to see in the surroundings

San Gimignano is at the center of the regional tourist heritage, 45 minutes by train to get to the central SMN station in Florence, 35 minutes by road to Siena, 20 minutes to Volterra, one hour to Lucca or Pisa.
San Gimignano is also close to countless minor centers of significant artistic, cultural, and environmental interest such as:

  • Certaldo 10 minutes – 8 Km
  • Castelfiorentino 15 minutes – 16 Km
  • Poggibonsi 15 minutes – 14 Km
  • Colle Valdelsa 20 minutes – 19Km
  • Casole d’Elsa 20 minutes – 22 Km
  • Pievescola 20 minutes – 22 Km
  • Monteguidi 20 minutes – 22 Km
  • Gambassi Terme 15 minutes – 13 Km
  • Vinci 60 minutes – 60 Km
  • San Miniato 35 minutes – 30Km
  • Sangalgano 50 minutes – 36 Km
  • Greve in Chianti 50 minutes – 39 Km
  • Massa Marittima 1.30 hours – 84 km across the panoramic road


Certaldo, the hometown of Boccaccio (Certaldo from the Latin Cerrus Alto) has a historic center of particular interest. The historic village, also called “Castle”, is gathered within the walls on which the ancient access doors to the village open: Porta Alberti, Porta al Sole, and Porta al Rivellino. You can access the village by going up the ancient and fascinating steep streets called Costa Alberti and Costa Vecchia, or from the more modern Via del Castello, or via the funicular that starts from Piazza Boccaccio.
The main feature of the medieval villages was the square, which overlooked all the powers of the time: religious, political, civil, and commercial power. Certaldo developed on a hill with an elongated and ellipsoidal shape that left no room for the ‘square’, whose function was taken on by the current Via Boccaccio which is overlooked by the Church, the palace of power (Palazzo Pretorio) and the Logge del Mercato (Palazzo Stiozzi Ridolfi), today closed but still visible in the walls. The current spaces that we can identify with the squares, at the time were only vegetable gardens, which would have served to provide food to the population in the event of a siege. The museum heritage is interesting and is made up of four structures: the house of Boccacio, the Museum of Sacred Art, the Praetorian Palace, the Nail Museum.

Immersed in the green Tuscan hills, Castelfiorentino is a charming town in the province of Florence. Located on a territory rich in naturalistic and historical itineraries, it represents today a pleasant discovery also from the tourist point of view. In an optimal position, it offers tourists the opportunity to stay in an artistically interesting location, with its numerous churches, its stately villas, the relevant frescoes by Benozzo Gozzoli, and those of the sanctuary of Santa Verdiana. The first nucleus, the Castelvecchio, it was built on the basis of an ancient settlement of Roman origin, called Timignano.
Feud of the Cadolingi and then of the Alberti Counts, in the XII century it was acquired by the Bishop of Florence and suffered the vicissitudes of the conflicts between the Church and the Empire and between Siena and Florence, of which it was an important outpost. Precisely for this reason it obtained the seat of the Podesta ‘, the privilege of the red lily on the white banner and the integration of the name, which from 1149 became Castelfiorentino. In 1260, after the battle of Monteaperti, peace between Siena and Florence was signed in Castelfiorentino.

Montaione is a country of ancient origins, rich in art, history, culture, and traditions; this is demonstrated by the numerous archaeological finds found nearby and which today can be admired together with an enchanting landscape typical of the Chianti countryside of Tuscany dotted with ancient villages, farms and old rural houses transformed today into comfortable holiday homes and farmhouses. In Montaione, San Vivaldo is known for the Sacro Monte, also called “The Jerusalem of Tuscany”, a place rich in history, art and religion. What sets San Vivaldo apart is its Sacro Monte or Gerusalemme di Toscana, a set of chapels and temples with terracotta groups and paintings from the Robbiana school of the 16th century. The construction works lasted from 1500 to 1515: the creator and builder of the Sacro Monte was Father Tommaso da Firenze. The Jerusalem of San Vivaldo is the exact reproduction, on a smaller scale, of the true Jerusalem of the end of the fifteenth century, even if oriented differently: an attempt was made to transfer the Holy Land to the site, materially and symbolically reconstructing the essential places of the Via Dolorosa.
A permanent exhibition is open in the premises of the former barn that illustrates the characteristics of the Sacro Monte. Also in the municipality of Montaione is Castelfalfi – whose name derives from ‘Castrum Faolfi’ – and its castle probably dates back to the year 754 following a settlement by the Lombards, even if the discovery of an Etruscan tomb in Podere Bianchi in the 1926 shows that the area was already inhabited in the Etruscan era.

Part of the castle, it passed to the bishop of Volterra in 1139, and in 1230 it submitted to San Miniato and then to Florence. In 1511 the Romanesque church of San Floriano was rebuilt and sacked in 1554 by the militias of Piero Strozzi at the time of the war between Siena and Florence that divided Tuscany.

In the Renaissance the Castle of Castelfalfi, which is located on a spur from which dominates the valley of the Roglio river in the heart of the lands of Tuscany, underwent various renovations until it was transformed from a military manor house into a villa, retaining its appearance up to the present day. Of particular curiosity are the cellars on two levels, where the first experiments of glazed vats dating back to the beginning of the twentieth century are found. For a long period the village was supported by a mainly agricultural economy, until the beginning of the 1900s where the tobacconist was built for the processing of the tobacco plant imported from America. The territory of Castelfalfi is remembered thanks to an important discovery in the 70s concerning the fossil remains of a whale found at the La Spina farm, now preserved in the Natural History Museum of the Municipality of Montaione. Lately, the Tenuta di Castelfalfi has been restored and used as a tourist residence. A sports complex was built consisting of a swimming pool and a tennis court, while nearby there is an 18-hole golf course set in a landscape of remarkable value, while a restaurant was built in the castle.

Poggibonsi (Podium Bonitii: Poggiobonizio) “poised in the province of Tuscany”, as Giovanni Villani defined it in his Chronicle of 1300, located in the Alta Valdelsa at the confluence of the main communication routes that cross Tuscany, apparently, it can only seem like a city modern and instead offers works of art and ancient monuments of great value and interest. Among these we remember the Palazzo pretorio a building from the end of 1200 beginning of 1300 and it was the seat of the civil power of Poggibonsi after the destruction of Poggiobonizio in 1270 and until the construction of the new Palazzo Comunale in 1862. The church testifies, in its structure the harmonic and gothic transition is essential and despite the repeated transformations undergone. The church of San Lorenzo degli Agostiniani di Lecceto, which had their convent for a long time, and is the site of the historical meeting between Charles VII and Girolamo Savonarola which took place, as an epigraph recalls, in 1495.
The building, after countless tragic events (suppression of the order, military occupation, transformation into a barracks first and then a hospital, bombings, etc. ..) has been intelligently and carefully restored and is offered to visitors in its harmoniously essential lines and with works of great value: an S. Nicola di Neri di Bicci, the fourteenth-century and venerated crucifix by Giovanni D’Agostino, the beautiful Madonna delle Grazie from the suppressed Oratorio del Piano, the Cassero della Fortezza di Poggio Imperiale and the imposing wall crown of the external perimeter of the Medici Fortress built in the early 1500s by the will of Lorenzo the Magnificent. The project was not fully completed and therefore the urban core provided inside was not built. Instead, the Cassero was built, with a pentagonal plan, which today, restored, dominates the surrounding hills. But the entire top of the hill of Poggio Imperiale, which overlooks the inhabited center of Poggibonsi, represents an extraordinary example in the process of settlement formation in central Tuscany.
The Municipality of Poggibonsi and the University of Siena wanted to create, on the hill, “The Archaeological and Technological Park of Poggio Imperiale” which offers tourists the opportunity to visit the different stages of settlement brought to light and to observe closely, during the periods of excavation, the work of archaeologists. The Park is in fact characterized by the presence of an ever-changing archaeological site, so much so that the Department of Archeology of the University of Siena has made it one of the points of excellence for its high-level research and training activities.

Colle Valdelsa
From the first settlements of the Neolithic dating back to the fourth millennium BC, and then to the Etruscan and then Roman ones, Colle di Val d’Elsa was born as a real city in the middle of the Middle Ages, to become one of the protagonists of the history of the free municipalities, of the struggles between Guelfi and Ghibellini, to then still definitively establish itself as an important industrial center. The inhabited area originally developed in three autonomous villages, distinguished by structures and planimetric configuration: the Borgo di Santa Caterina, the Castello di Piticciano and the Piano. The first two settlements are the oldest, privileged seats of the city hegemonic groups, and are located on the same hilly ridge in the East-West direction and separated by a large valley, dominate the area of ​​the valley floor where the third “village” stands, the one of the Plan, more recent for urban diffusion and always used for production activities. Although presenting the territory of Colle great archaeological finds, dating back to the fourth millennium BC, the first documents, where Colle di Val d’Elsa is named, date back to the tenth century, but it is from the end of the twelfth century that the town gradually acquired autonomy and political identity: the first documented municipal statutes date back to 1307.

Casole d’Elsa
Casole d’Elsa, an ancient Etruscan settlement, as evidenced by the numerous tombs found, is a village located on the back of a hill that gives the visitor a very suggestive panoramic view. In the 11th and 12th centuries it was a fiefdom of the Bishops of Volterra. Passed in 1260 under the dominion of the Sienese, being a place of strategic interest, to defend it from external attacks it was necessary subsequently to erect new fortifications. including two round towers on the eastern side still in existence. Casole thus assumed the characteristics of the “walled tower”, that is, surrounded by walls preserved to this day. The walls of the town of Casole have an ovoid shape, with an extension of the axis greater than about 400 meters and a width of about 130. The two ancient access gates now no longer exist; the north one took the name of Porta ai Frati; the one to the south, called Porta Rivellino, can only be seen on old photos taken before it was destroyed by the Nazis during the Second World War. On the eastern side, however, there are still two round towers built-in 1481 by Francesco di Giorgio Martini, who was in charge of strengthening all the fortifications.

Pievescola stands on the slopes of Montagnola, not far from the valley floor of the Via Maremmana. Its parish church, dedicated to San Giovanni Battista, was founded at the beginning of the century. XI by the countess Ava di Montemaggio, who shortly before had founded Abbadia a Isola. It was probably part of the Suvera community. It has a basilica plan with three apses with naves divided by quadrangular pillars with attached half-columns. The facade, with a double lancet sail bell tower built at the rear, bears an architrave portal surmounted by a filled arch and above a beautiful trifora in yellow marble of Pisan Lucchese taste, which can be referred to the living room of the Pisan master Bonamico when he was busy in the parish church of Mensano.

Monteguidi was an ancient Aldobrandeschi castle, which in the middle of the century. XIII was already subjected to Siena. It had an elongated shape in a north-south direction, with a maximum size of about 130 meters, while the transverse one did not exceed 40 meters. Unfortunately, today there is almost no trace of the ancient walls, while the two doors at the ends of the major axis are still preserved. Of the northern gate only a round stone arch remains. The southern door is well preserved and consists of an external stone arch and a deeper vaulted one, in brick from the inside. Almost every trace of the walls has been lost, except for a very short stretch of the eastern ones, which can be found almost behind the church of S. Andrea. Along the central street, via Cavour, some houses are lined up that conserve evident medieval structures and two stone towers. The Church of S. Andrea and S. Lorenzo, located at the north gate, is Romanesque. Transformed by the renovations undergone in various eras, it preserves the ancient building, the brick and stone arch surrounded by a terracotta frieze and the small portal on the left side, with the stone architrave, supported by two shelves.

Gambassi Terme
Water and well-being, art and nature, culture, and gastronomy: three combinations that make Gambassi Terme the ideal place for a stay dedicated to the regeneration of body and mind. Gambassi is in fact in the heart of the most authentic Tuscany, in that glimpse of Valdelsa where the gaze is lost among the gentle hills, crowned by vineyards, olive trees and cypresses. Ancient land, inhabited by the Etruscans and Romans, the town was a staging post for the travelers and pilgrims who traveled the Via Francigena in the Middle Ages. Since the 14th century Gambassi became a glass production center and its “bicchierai” were in demand throughout Italy. Of this flourishing artisan activity, recent archaeological traces in the municipal area have recently been found, today gathered in a permanent exhibition. It is in this fascinating context that the spa and wellness center “Acqua Salsa di Pillo” rises. Wrapped in an enchanting park of centuries-old plants, the spa building was completely renovated between 2002 and 2003 and now offers a much more welcoming and functional environment, offering customers a wide range of spa, therapeutic, and aesthetic.

San Miniato the noble city
The title derives from its particular geographical location. San Miniato is located along the Via Francigena, which connected northern Europe to Rome in the Middle Ages, an uninterrupted flow of men, armies, trades, ideas, and cultures. San Miniato is a land of Etruscan and then Roman settlement, as evidenced by the excavations of a necropolis of the third century BC. in Fontevivo and those of a Roman villa in Antonini, whose finds are visible in the Archaeological Museum of Florence and in a small part in the Civic Museum. The original nucleus of the city dates back to the eighth century, when seventeen Lombards, according to the original document of 713 preserved in the Archiepiscopal Archive of Lucca, built a church dedicated to the martyr Miniato. The city is therefore of Germanic origin and from the Middle Ages it will be known as San Miniato al Tedesco. Over five centuries San Miniato grew as a medieval bastion, since Otto I of Saxony in 962 made it one of the imperial centers, up to Frederick II of Swabia there in 1218 built his castle, and destined to the collection of taxes for central Italy. San Miniato, as the Swabian power declines, becomes a free municipality. The city extends with large convents, schools, institutions, and hospitals. The municipal statutes, preserved in the historical archive, testify to its independence and luck. Only at the end of the 14th century did San Miniato have to submit to the nascent Florentine Lordship. It will again be a German, Mary Magdalene of Austria, wife of Cosimo dei Medici to privilege San Miniato, making it a bishopric in 1622. A large marble statue will be erected for gratitude. Unfortunately destroyed at the end of the eighteenth century by the Jacobins of San Miniato during the French Revolution, today only a powerful fragment remains, located near the Franciscan convent. Strong is the development of the city in the following century. The diocesan see enriches it with the Sanctuary of the Most Holy Crucifix and the great seminary. Cultural life is fertile and creates study and culture academies, such as that of the Affidati and then of the Euteleti. At the end of the nineteenth century San Miniato is a city now defined. World War II will inflict a heavy blow when the German army undermines and destroys the fortress of Federico II and a large part of the medieval quarters, but the reconstruction will be rapid: in 1957 the fortress was rebuilt from the ruins to indicate the rebirth from the plain of the city.

Vinci birthplace of Leonardo Da Vinci
The primitive construction of the castle, still dominant in Vinci, dates back to the early Middle Ages and is known in popular tradition as the “ship’s castle” for its elongated shape and the tower which refers to the shape of a sailing boat. Around the year one thousand the village became the possession of the Guidi Counts, who dominated its fortunes until August 12, 1254, when Vinci was subjugated to Florence and transformed into a municipality. Located on the western border of the state, Vinci was the subject of contention by the enemies of Florence and directly experienced the turbulent events that tormented the political life of the capital. Under the walls of the castle the soldiers led by Uguccione della Faggiuola (1315), Castruccio Castracani (1320-26), Jona Hakwood, called Acuto (1364), head of the British venture companies in the pay of Pisa, took turns. After numerous vicissitudes and modifications of the original structure, the Castello returned to the ownership of the Municipality of Vinci in 1919. In Anchiano, on 15 April 1452, Leonardo was born and spent the years of his childhood in Vinci. Of particular interest are the Leonardian Museum, the Historical Museum of hunting, and the territory. Medici Villa, Cerreto Guidi.

San Galgano
The complex consisting of the Hermitage or Rotonda di Montesiepi and the ruins of the large Circestense Abbey of San Galgano is one of the most suggestive found in Tuscany. In the Rotonda di Montesiepi there is the sword of San Galgano stuck in the rock. Built between 1182 and 1185, above the hut on the hill where San Galgano lived his last year of life and right there where he had stuck his sword in the rock, the Rotonda di Montesiepi was originally the Tomb of the Saint who was buried in the north of the sword as if to see, through the entrance door, Chiusdino. Only in 1220 (or 1218?) Was the construction of the great Abbey downstream started. The construction works last until 1268, when it was officially consecrated by the Bishop of Volterra Alberto Solari. After a hundred years of great splendor until 1364 followed the slow decline given by the unfortunate practice of the Commenda. One fact above all: in 1550 the Commendatario Girolamo Vitelli came to sell (after the jewels and who knows what else) the lead roof. Despite some attempts to restore the convent at the end in 1789, after the Rotonda di Montesiepi was elevated to Pieve, the great abbey was deconsecrated and definitively left to ruin. While the Rotonda di Montesiepi brings us, with its Sword in the Rock, to the saga of King Arthur, the great Abbey reserves us, with its Sacred Geometry, other surprises, both “musical” and “Egyptian” and on the Holy Grail.

Castellina in Chianti
Of Etruscan origin, Castellina in Chianti played a primary role for its key position of connection between the southern Etruscan cities and the North. In 1200 it passed into the sphere of influence of Florence, after being a fiefdom of the Lords of the Trebbio, of which it was a military garrison, above all for its geographical proximity to Siena, historical enemy of Florence. In this period it is the capital of the Lega del Chianti, including the territories of Gaiole in Chianti and Radda in Chianti, whose emblem is a black rooster, the same reproduced in the emblem of the Municipality of Castellina. In 1500 it definitively became part of the Grand Duchy of Tuscany, losing its strategic-military character and becoming an agricultural center: its hills were covered with farms and farmhouses. The historic center has a medieval structure which is testified by Via delle Volte, a covered road leaning against the ancient walls: a covered path that runs along the east walls, very suggestive. which follows the ancient pomerium, a public space of archaic origin adjacent to the walls, with sacral and military security functions. Originally discovered, it was covered by the backing of private houses to the walls themselves when they lost their defense function. Going along the main road from south to north, you can see Ugolini palace, formerly Squarcialupi, on the right. with a large facade with three doors with encrusted sandstone drafts, eight arched windows on the first floor corresponding with square windows on the second. On the facade are two stone coats of arms of the Ugolini family. The adjacent Palazzo Bianciardi has three floors and two orders of square windows framed in pietra serena. Above the entrance is the Medici coat of arms of Pope Leo X (Giovanni de ‘Medici, son of Lorenzo the Magnificent, Pope from 1513 to 1521) who refreshed himself here during his passage in 1513.

Greve in Chianti
The oldest inhabited center, from which the center of Greve originated, is located on the current hill of San Francesco, mentioned in an 11th-century document for a donation of S. Bernardo degli Uberti to the Monastery of San Salvi. Later it was the site of an ancient hospital and, from the end of the fifteenth century, it housed a small monastic settlement of the Franciscan Order (from which it took its name), now transformed into the seat of the Museum of Sacred Art. Greve in Chianti was born on the edge of the important communication networks that led to via Volterrana and via Francigena. On the other hand, the roads of the area made it easy to reach Florence and, through the current Passo del Sugame, the Arno valley upstream of Florence, where there are important market places (such as Figline Valdarno). It was precisely this character of openness towards various commercial landings that determined the birth of the market of Greve, the current Market Square, in the center of a densely populated area, already rich in parish churches and rural churches and dotted with castles and villages feudal, which after the conquest and subsequent transformation by the Florentines have become stately homes, villas and farmhouses. Florentine Chianti was a valuable area from an agricultural point of view: among other things, a highly appreciated wine was produced, mentioned in documents from the 14th century, which cheered the canteens of the wealthy Florentines. The intermediate position between Florence and Siena, in a period of great cultural, artistic and economic growth of the two main cities of Tuscany, had important consequences for the development of the entire territory of Grevigiano, to which the regular presence in the country residences also contributed, of a qualified leading class, represented by the main Florentine families. The oldest part of the village gravitates around the convent of San Francesco and the market square: this structure will remain substantially intact until the nineteenth century. Only after the unification of Italy, with the assignment of the seat of the municipality, the old “market in Greve” will become the most important center of the valley.

Massa Marittima
Massa Marittima is a city of art nestled between the Metalliferous Hills, surrounded by the Maremma countryside and rich in historical, environmental, and architectural beauties inherited from a thriving past. From the medieval village, to the new city, you can walk the ancient and steep alleys that intertwine in the historic center and go up to the upper part of the village; here it is easy to find suggestive and characteristic corners and panoramic points overlooking the valley to the sea. Many of the most significant places are enclosed by the town square: the marvelous Cathedral of San Cerbone, the Palazzo Comunale, the sources that surround the famous fresco of Abundance, and the Palazzo del Podestà, home to the archaeological museum. Going up to the New Town you will find buildings dating back to the 13th century: the complex of San Pietro all’Orto, with the cloister of Sant’Agostino, the Torre del Candeliere and the Fortezza Senese. Tourism is becoming the driving activity of the town: in addition to the historical-monumental heritage and museums, the city offers various hiking opportunities, from trekking to cycling tourism, to horse riding. The city is surrounded by the typical vegetation of the place: from the thick and low scrub to the laurel and broom bushes, up to the stems of the holm oaks and strawberry trees. The main events that take place every year in the city are particularly interesting and suggestive for tourists and visitors: the Balestro del Girifalco, the Toscana Fotofestival, Lirica in Piazza and Calici under the stars.

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