Self-Guided Tours - Tuscany

Attractions and sites of interest on or close to the routes

• Abbazia di Monte Oliveto Maggiore
  The huge pink brick buildings of this famous abbey nestle among the cypress trees in a landscape of eroded hills Mount Oliveto is the mother-house of the Olivetians, a congregation of Benedictine monks founded in the early 14th century
  
  
• Arezzo
  The old town is built in terraces on a hill crowned by a citadel, surrounded by a fertile basin planted with cereals, fruit trees and vines. A large number of tower houses contribute to the picturesque aspect of the town.
  
  
• Bagno Vignoni
  This hamlet has long been renowned for its spring water which was reputed for its effectiveness in the treatment of arthritis and rheumatism as far back as Roman times. The houses cluster around an old bathing pool flanked by Saint Catherine’s Portico – the saint is reputed to have come here at the end of her life.
  
  
• Buonconvento
  Standing at the confluence of the Arbia and Ombrone rivers on the via Cassia, the Roman road between Siena and Rome the town is built entirely of brick and enclosed within 14th century walls. Emperor Henry V11 died here in 1313.
  
  
• Castellina in Chianti
  An important centre of the Chianti League. Magnificently positioned in beautiful countryside, the town still has its medieval square plan and 15th and 16th century houses dominated by the crenellated tower and castle keep.
  
  
• Castiglion Fiorentino
  Occupying the site of an Etruscan settlement, the town is set on a slope above the Chio, a tributary of the Chiana. Fought over throughout the Middle Ages because of its strategic position, it finally fell to Florentine rule in the 1384.
  
  
• Colle di Val d’Elsa (Tuscany Extended only)
  Developed between the 10th and 13th centuries, the town consists of three distinct sections. The lower Colle Bassa (terziere di Piano) produces glass and crystal. The other two sections (terzieri di Castello e Borgo) form Colle Alto and feature splendid architecture of medieval origins with Renaissance additions.
  
  
• Cortona
  The town (of “Under the Tuscan Sun” fame) occupies a remarkable site on the steep slope of a hill overlooking the Chiana Valley not far from lake Trasimeno. It belonged to the league of 12 Etruscan towns before coming under the control of Rome. Cortona has retained its medieval town walls commanded by the huge citadel and the town has barely changed since the Renaissancce, with fine mansions and steep paved streets leading to irregularly shaped squares lined with arcades and impressive public buildings.
  
  
• Lucignano
  This peaceful village in the Val di Chiana has an unusual shape, the main street rising in spirals before entering a picturesque maze of medieval streets.
  
  
• Montalcino
  This hillside town, which still has part of its 13th century walls and its fortress, is known throughout Italy for its excellent red wine, Brunello, a high quality vintage from a restricted wine-growing area. Every autumn during the Thrush Festival, the four districts of the town recall the past with a parade in medieval costume and an archery contest.
  
  
• Montepulciano
  An attractive Renaissance town occupying a remarkably picturesque setting on the top of a tufa hill that separates two valleys. Poets have long sung the praises of its ruby-red wine (Vino Nobile). Antonio da Sangallo the Elder of the famous family of Renaissance sculptors and architects bequeathed some of his most famous works to the town.
  
  
• Monteriggioni (Tuscany Extended only)
  The town with its superb round circle of towers greatly impressed Dante, who described it in his Divine Comedy. The citadel was erected by the Sienese. The medieval atmosphere and intact fortifications arranged make the town the most significant example of a “walled land” in Sienese territory.
  
  
• Monte San Savino
  The medieval town has a thoroughfare lined with fine historic buildings that links the two gates set within the walls of the old stronghold. The sculptor and architect Sansovino (1470 – 1529) was born here.
  
  
• Monticchiello
  This medieval village, surrounded by walls dotted with crenellated towers, is riddled with lanes and charming little squares. The village church has a pentagonal staircase leading to its austere Gothic doorway.
  
  
• Murlo (Tuscany Extended only)
  A tiny medieval village consisting of several buildings in a single row of houses backing onto the town walls. Famous also today for Etruscan archaeological discoveries made in Poggio Civitate nearby.
  
  
• Pienza
  The town displays a stunning unity of style, especially in its main square, and is a perfect example of Renaissance town planning as commissioned by Pope Pious II, a humanist philosopher who wanted to build the ideal town.
  
  
• San Gimignano (Tuscany Extended only)
  Medieval walled town with 14 towers in an enchanting setting. The towers (there were once 72 of them!) were built with the immense wealth of the town’s merchant classes.
  
  
• Sant’ Antimo
  The former abbey of Sant’Antimo lies at the foot of the village of Castelnuovo dell’Abate and has preserved its solitude in the depths of the delightful Tuscan landscape.
  
  
• San Quirco d’Orcia
  The old town still has its 12th century walls and its huge gates. The town gained importance early in the Middle Ages because it straddled Via Francigena – the road that passed through the Orcia Valley linking Rome and the North of Italy.
  
  
• Siena
  A medieval city par excellence, crammed with rich treasures of art and architecture, Siena has always held a unique fascination for the visitor. It hosts “The Palio” – the world-renowned and distinctly mad horse race The city is overlooked by the elegant tower of the Palazzo Pubblico and the black and white stripes of the vast cathedral. The city’s motto, inscribed above the Camollia Gate is “Cor magis tibi Seni pandit" – "Siena opens its heart even wider to you.”
  
  
• Trequanda
  This small hilltop village has retained some sections of its crenellated walls and a few remains of Cacciaconti Castle including a huge round corner tower. The 13th Century Church of San Pietro has a very unusual rustic façade with an alternating checkerboard design of white travertine and brown-ochre local stone.
  
  
• Volterra (Tuscany Extended only)
  The city standing 550 m above sea level dominates the Cecina Valley. It was one of the twelve Etruscan League towns and is a treasure chest of Etruscan, Roman, Medieval and Rennaissance art. One of the town’s main industries is the working of alabaster, a craft which dates from the 8th century BC.

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