the first leg of the itinerary leading to the discovery of the territory is siena, the city famous for its palio and listed as world heritage by unesco for its singular artistic heritage.
the historical center is dominated by piazza del campo, one of the biggest medieval piazzas. it is shell-shaped and is the stage for the famous corsa del palio (silk banner horserace). here stand monuments of great value, such as the 13th-14th-century palazzo pubblico (the town hall), a true jewel of the gothic and home to the civic museum; the piazza chapel, upon which stands the bell tower, torre del mangia, and jacopo della quercia's marvelous gaia fountain (in actual fact, the piazza holds a copy, while the remains of the original are preserved in the museum complex of santa maria della scala).
one of the city's numerous art treasures is the duomo (12th-14th century), one of the highest expressions of romanesque-gothic art, abounding in sculptures, paintings and works of architecture, also home to the opera metropolitana museum, exhibiting masterpieces by famous artists such as duccio di buoninsegna, ambrogio lorenzetti and taddeo di bartolo. two other of the city's art treasures are the imposing medici fortress in red brick, commissioned by cosimo i in the mid-16th century and the elegant loggia della mercanzia, a transition architectural work from gothic to renaissance style.
a place of great devotion is the house and sanctuary of st. catherine of siena, the patron saint of italy and europe. the structure, built around the house, comprises chapels and cloisters richly-decorated by various artists.
not to be missed is the pinacoteca nazionale housed in the elegant palazzo buonsignori, featuring a collection of 13th-16th-century works of the sienese school.
in addition to the marvelous city of siena, not to be missed are the crete and the natural and cultural artistic park of val d?orcia, listed as a world heritage site by unesco for the beauty of its landscape and an inspiration to many renaissance artists. here stands a city of particular importance, pienza.
it too is recognized by unesco as a world heritage site for the wealth of its monuments and its rational organization of space and perspective. pienza is the ?ideal city,? created upon the wish of pope pius ii for a city built according to renaissance ideals.
in the val di chiana area lie other delightful towns. montepulciano is located upon a hill from where it dominates the valley, with its rising and falling slopes in a typically-medieval atmosphere. chianciano terme is important for its beneficial waters that were famous as far back as etruscan times, and is home to the beautiful museo archeologico delle acque (water archaeological museum). chiusi is a small town with an internationally-reputed etruscan museum.
in val d?elsa, charming are monteriggioni and san gimignano, also called the "city of towers" for its numerous towers and tower-houses that render its skyline quite unique; it was the symbol of medieval mercantile power. this characteristic medieval borgo, under the tutelage of unesco, boasts a remarkable artistic legacy, including the marvelous collegiata (13th century), the gothic-romanesque st. augustine's church and the palazzo del popolo - site of the civic museu, upon which stands the torre grossa (big tower).
other characteristic towns abound in the sienese territory: of particular ntoe is montalcino, home to the famous brunello wine, and the nearby st. antimo's abbey, a splendid example of romanesque-tuscan style with lombard influences.