Siena is the opposite of Florence in nearly every way that matters, and the Sienese would like you to remember it. It sits on three ridges in southern Tuscany, a compact medieval city of brick and stone in warm reddish-brown tones, and at its centre lies the Piazza del Campo, a vast shell-shaped square sloping down to a tall brick tower, the Torre del Mangia, about a hundred metres high. Twice each summer, on the second of July and the sixteenth of August, the square is covered with earth and ten riders from the city's districts, the contrade, race bareback around it in the Palio, a dangerous, chaotic event that lasts about ninety seconds and is felt by the whole city as a matter of honour.
The seventeen contrade, each with its own emblem, colours and fountain, dominate local life, and you will see their flags hanging in the streets. The cathedral, made of striped black and white marble, has a floor of inlaid scenes and a library of painted manuscripts that dazzles. The city was a rival to Florence in the Middle Ages, a banking power and home to its own school of painting, and its bank, Monte dei Paschi, founded in 1472, claims to be the oldest in the world still operating. Local food includes panforte, a dense spiced cake, and ricciarelli, soft almond biscuits.
For riders, Siena is the starting point for a famous scenic ride. South of the city, the roads wind through the Crete Senesi, a landscape of pale clay hills, and then into the Val d'Orcia, a UNESCO site of rolling fields, cypress-lined lanes and hilltop towns such as Pienza and Montalcino. Surfaces are generally good, with gentle curves and wide views, and the white gravel roads, strade bianche, add some adventure for those who like it. Spring, when the fields are green, and late September, when the grapes are ripe, are the best times. July and August are hot, and tourist traffic is heavy.
Be careful in the old city, because much of it is a restricted traffic zone where unauthorised vehicles can be fined by camera, so park outside the walls and walk in. Fuel stations and workshops are on the ring roads, and plenty of cafés and trattorias are in the historic centre. Stay for sunset in the Campo, when the brick turns gold.