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You may find it helpful to view and print off a copy of the regional map and cross reference with the description below. Letters in brackets refer to the relevant cycling routes.
(Letters in brackets refer to the relevant cycling routes)
The iron Donkey Tuscany region is centred on the beautiful city of Siena, the trailhead for most of the itineraries.
Siena’s Gothic brick-built hill town contrasts with Florence’s Renaissance marble. The city, perched on three steep hills and enclosed by extensive walls is crammed with art and architecture. The elegant tower of the Palazzo Pubblico and the black and white stripes of the vast cathedral rising above the rooftops, are visible for miles around. The city is certainly worth a full day – or two if you have the time. The Piazzo del Campo, one of the most beautiful piazzas in Italy, is the setting for the renowned biannual Palio horse race. The passage-lined Via Banchi di Sopra is Siena’s main passeggiata for evening promenading . (A, F, H, M)
Le Crete (the translation is “craters”) south of Siena is an extraordinary semi – desert landscape of rounded hills devoid of trees. The hills, made bizarrely uneven by erosion furrows and outcrops of greyish clay are coloured a myriad of different shades by the sunlight and shadows - shades that vary with both the season and with the time of day. Tiny roads wind through the fields and along hill crests to connect ancient farmhouses and tiny medieval villages. This area abounds with ancient Roman and Etruscan archaeological sites. (F, H, G)
The small town of Asciano, in the heart of the Crete, still has many of its old medieval palaces and various towers, including the guard towers of the outer walls, which now lie inside the modern-day town. There is a variety of unusual mixed Romanesque and Gothic architectural forms. The tiny medieval village of Murlo is famous for exhibitions of Etruscan archaeological discoveries made in nearby Poggio Civitate. In Buonconvento’s historic centre the Museo d’Arte has Sienese school works by Duccio, Sano di Pietro and Matteo di Giovanni. (F, H)
The Benedictine monastery of Abbazai di Monte Oliveto Maggiore stands on a scenic rise in a wooded park. The remarkable renaissance frescoes by Sodoma and Signorelli in the abbey’s main cloister are the main incentive to pedal up the hill! (H)
The Val d’Orcia, extending south from Le Crete to Monte Amiata, is a landscape of gentle, carefully-cultivated hills occasionally broken by gullies or patches of erosion. Possibly no other region conjures up such classical images of Tuscany - the hamlets and hilltowns, terracotta rooftops, swaying cypress and golden valleys, vineyards and olive groves all contribute to the overall picture. The ancient Via Francigena linking Rome and the north of Italy passes through the valley. (I, J)
Towns and fortified villages have been built on the higher hills that overlook the Val d’Orcia. San Quirico d'Orcia with its 12th century walls and huge gates, gained importance as a staging post on the Via Francigena. Duke Diomede Leoni, who ruled San Quirico from about 1570 onwards, built the splendid Horti Leonini gardens inside the fortified walls of the town. (I)
The fortified town of Montalcino, settled first by the Etruscans and then by the Romans, is situated on the summit of a hill that has a commanding view of the surrounding valleys. It once flew the flag of the Sienese Republic, but aside from the important historical and artistic attractions of the town, it is known throughout the world as the home of Brunello, an exceptional wine that was developed in the middle of the 19th century when Ferruccio Biondi Santi decided to use only Sangiovese grapes. (G, H, I)
Near Montalcino, set amidst vineyards and olive groves of the Starcia Valley, is the Abbazia di Sant'Antimo, one of the most attractive examples of 12th century monastic architecture. The magnificence of the abbey, built from a particular kind of veined travertine that makes it luminous, is enhanced by the beauty of the surrounding countryside. The Augustian monks who tend the church sing Gregorian chant at mass. (C)
Pienza was constructed over the older settlement of Corsignano on the orders of Pope Pio II, a native of the town. He awarded the commission for the work to Rossellino who employed the best artists of the period on this massive project. The result was a small gem of Renaissance architecture. (J)
Bagno Vignoni has been known for its thermal springs since ancient times and the village has a truly unique atmosphere. The main piazza is an enormous bath filled with steaming water. Visitors to the original thermal bath included Pope Piccolimini, Lorenzo il Magnifico, and Santa Caterina da Siena, to whom the gallery and chapel flanking part of the piazza are dedicated. The modern-day village has baths equipped for thermal cures. (D)
The village of Monticchiello, enclosed by walls dotted with crenellated towers, is riddled with lanes and charming little squares. From the village church there is a superb view of the Orcia Valley.
The town of Castiglione d'Orcia, situated on a spur that dominates the valley was developed beneath the imposing bulk of the ancient Rocca degli Aldobrandeschi, from which there are wonderful views of Monte Amiata to the south. (C)
The charming hill town of Montepulciano produces Tuscany’s second greatest wine – Vino Nobile. (I, J, K)
The Val di Chiana, south of Arezzo and lying between the Val d'Orcia and the Val Tiberina, has long been inhabited, as shown by the prehistoric graffiti found in caves on Monte Cetona. It gets its name from the Chiana river, and the valley is a natural communications route between the provinces of Arezzo and Siena. The present-day appearance of the Val di Chiana is the result of marsh drainage and reclamation that was started by the Romans and carried on right through to the 20th century. Leonardo da Vinci drew up a map of the area at the beginning of the 16th century, which showed that the valley was occupied by a large lake running north-south; the cities and villages in the hills on either side of the lake communicated by means of the ford at Valiano, a small village which still exists, and Siena and Florence fought for control of it on a number of occasions. Nowadays there are just two remnants of the original large lake, the Lago di Chiusi and the very small lake at Montepulciano. The valley floor is a picturesque patchwork of sunflower, tobacco and corn fields. (J, K, L)
Cortona, perched high above the Chiana Valley started out as an Etruscan settlement. The town is a treasure trove of ancient tombs and Renaissance art. The centre has steep streets and several interconnecting squares, and there is an impressive 16th Century Medici fortress. The views from the ramparts over the valley far below are wonderful, and a well earned reward for the effort expended in getting there! (L, N, O, P)
The small ceramics town of Monte San Savino has a pottery museum, and the Santa Chiara church has early works in terracotta by native sculptor Andrea Sansovino. (K, M, N)
The Alpe di Catenaia rise between the Val di Chiana and the Tiber valley to the east. Historic Sansepolcro stands at the boundary between Tuscany and Umbria - the medieval town’s reputation is built around Buitoni pasta and native genius Piero della Francesca. The Museo Civico houses Piero’s “Madonna della Misericordia” and the compelling “Resurrection”. (P, Q)
Val d’Elsa is to the north west of Siena. The town of Colle di Val D’Elsa has a lower and an upper town. Colle Alta – the upper town – is of great medieval architectural interest. In the modern lower town shops sell locally made crystal glass. (A)
San Gimignano is the hill town that is most evocative of the Middle Ages. Fourteen of the original seventy towers are still standing in this medieval Manhattan, and the town contains an amazing wealth of 14th and 15th century art. There is also an excellent local white wine! (A, B)
The world’s greatest alabaster craftsmen can be found working in Volterra, the loftiest hill town in Tuscany. The stony medieval streets of the town rise 555m above the valley. Volterra was one of the key cities in the Etruscan Dodecapolis confederation, and the museum is filled with finds unearthed as ongoing erosion at one end of the town exposes ancient tombs. (B)
To the south of Voterra the Metalliferous Hills, clothed in chestnut, beech and evergreen oak forests, are rich in iron ore and other minerals. (B)
The Etruscan Coast stretches from Livorno south to the Piombino promontory. It is a mix of rocky shore and sandy beaches backed by pine forest. The resort of Marina di Bibbona has several fine beaches, and a fort built by the French in the 18th century. (B, C, D)
Bolgheri is well known for its wines. Close to the village is a wildlife sanctuary which is of special interest to bird-watchers. (C).
Offshore, the island of Elba is an hour’s ferry ride from the port of Piombino. The island is an incredible mosaic of natural scenery – gulfs, headlands, precipitous coastline, sandy bays, wooded mountains and terraced vineyards all surrounded by the deep blue Mediterranean.
Straddling Tuscany’s southern boundary with Lazio are the volcanic mountains of central Italy – the highest being Monte Amiata at 1750 m. Between these mountains and the sea is the Maremma – the Etruscans and Romans in turn drained its swamps to create richly fertile farming land. After the fall of the Roman Empire the region fell into disuse and for a long period was virtually uninhabited. The relative lack of intensive farming means the region is still rich in wildlife – from butterflies and orchids to tortoises and porcupines. (D)
Massa Marittima is two hill towns in one. The “Old Town” is built around a triangular piazza with the Duomo and the palazzo, while the upper new town was founded in the 14th century by the conquering Sienese. The “new” fortress has sweeping views over the hills. (D, E)
To the east of Massa Marittima the picturesque villages of Montemassi, Sassofortino and Roccatederighi dot the tops of hills to the west of Roccastrada. (E)
This ruined Cistercian Abbey of San Galgano is sited in a superb woodland setting. On a hill above the abbey is the beehive-shaped chapel of Montersiepe, built around 1185 on the site of Saint Galgano’s hermitage. St Galgano’s sword is embedded in a stone inside the door of the circular oratory. (E)
In the piazza at the entrance to the village of Monticiano the late-Romanesque church of Sant'Agostino has a splendid Baroque interior. In the adjacent former monastery, the chapter house is decorated with a cycle of frescoes depicting the Passion. (E, F, G)
To the north of Siena is Florence and you can add on a day or two to either end of your bicycle tour to explore this wonderful city – the cradle of the Renaissance. It is also possible to start in Florence and ride to Siena as an alternative start to your cycling trip.
The Chianti region between Siena and Florence is a magical landscape of olive groves, vineyard- blanketed slopes, fields and wooded maquis with rows of cypresses climbing towards hilltop farmhouses, turreted castles and stone villages. Chianti has always been a wine-producing area (there is evidence of viticulture back to Etruscan times), and the beauty of the landscape is inextricably inter-related with the work of man. (U, V)