Siena

The fan-shaped square tilts down towards the town hall, its brick paving split into nine wedges for the old Government of Nine. People simply sit or lie on the ground. The Fonte Gaia carvings at the top are copies; the originals are in Santa Maria della Scala.

On 2 July and 16 August earth is laid round the Campo and ten contrade race horses. Three laps take little more than a minute, but trial runs and parades fill the preceding days. A spot in the centre means getting in hours before the start, with no toilets.

A 102m brick tower beside the town hall, climbed on foot up a narrow stair. Small groups go up at set times, so unless you buy a ticket in the morning your turn may never come that day. In rain the climb is shut.

A cathedral of black-and-white striped piers, its entire floor covered by fifty-six inlaid marble panels. To spare them wear they stay covered most of the year and are bared for just a few weeks, so seeing them all means timing your visit.

A room off the cathedral's left aisle, where Pinturicchio painted the life of Pope Pius II across ten wall panels. The frescoes date from the early 16th century yet look freshly painted. A Roman statue of the Three Graces stands in the middle.

A lone facade wall from a far larger cathedral Siena began and abandoned when the Black Death struck in 1348. A tight spiral stair in the cathedral museum climbs to its top, over the Campo and the city's roofs. Up there you wait your turn in single file.

Facing the cathedral, this hospital cared for pilgrims and foundlings for nearly a thousand years and took patients until the 1990s. In the Pilgrims' Hall, 15th-century frescoes show the sick being washed and babies nursed. Archaeology fills the floors below.

Each of the seventeen wards has an emblem such as the tortoise, snail or she-wolf, and wall flag holders and small fountains show which one you are in. Ward museums usually open only near Palio time or by booking. Evening ward dinners set tables in the street.

A hill village northwest of Siena where fourteen towers, raised by rival medieval families, still stand. The Siena bus needs just over an hour, and by day tour groups choke the lanes, so staying into the evening is calmer. Its white wine, Vernaccia, is famous.

Pope Pius II rebuilt his native village as an ideal town, and from the walkway along its walls the cypress-lined Val d'Orcia hills roll away without end. Lanes bear names like Kiss Street and Love Street. Buses are scarce, so a car makes life easier.

Duccio's Maesta altarpiece, finished in 1311, fills a whole room. The day it was done, the story goes, citizens rang bells and carried it in procession from his workshop to the cathedral. One pass admits you here, to the cathedral and to the baptistery.

Built into the ground beneath the cathedral's apse, so you reach it down a stairway beside the cathedral to a lower square. Ghiberti, Donatello and Jacopo della Quercia were among the sculptors who shared the bronze font in the middle.

In the Campo's town hall museum, Lorenzetti's Good and Bad Government, begun in 1338, covers three walls of the council room. Traders and dancers crowd the good side; the bad side shows only ruins. Outside the painted gate, farmers plough Sienese fields.

Sienese paintings on gold ground from the 13th to 15th centuries, hung in date order across two joined Gothic palaces. It lets you set the city's ornamental, graceful line against Florence's. Visitors are few, so it is quiet.

A vast plain brick church on the ridge's western tip, where St Catherine of Siena prayed. A side chapel shrine holds her head, with her thumb kept separately. From the forecourt the cathedral and tower line up side by side.

A 13th-century fountain house in the dip below San Domenico, its red-brick front made of three pointed arches. Tunnels dug into the hill gathered the water, which tanners once used. St Catherine's birthplace is in the lane just above.

A tiny hilltop village north of Siena, ringed by a 13th-century wall set with fourteen towers. Dante compared them to giants standing in a circle in his Inferno. A ticket lets you walk part of the wall-top path.

A Renaissance hill town strung along a narrow ridge over the Val di Chiana; town hall and cathedral face off across Piazza Grande at the top. Palace cellars tunnel under the main street, and wine shops hold tastings in them. Buses from Siena take an hour-plus.

A roofless Gothic abbey, walls and pillars standing on grass under open sky. In the Montesiepi chapel on the hill above, a sword the knight Galgano is said to have driven into rock in 1180 sits under a glass cover. Allow nearly an hour southwest by car.

A Benedictine abbey still home to monks, in woods among the grey clay hills of the Crete Senesi. Thirty-six scenes from St Benedict's life, most of them by Signorelli and Sodoma, run round the great cloister. The shop sells liqueur and honey made by the monks.