Siena sits on three ridges in the heart of Tuscany, a red-brick medieval city that has hardly changed its shape in seven hundred years. At its centre is the Piazza del Campo, a sloping, shell-shaped square paved in brick and divided into nine sections, a reminder of the Council of Nine that governed the city in its golden age. The Palazzo Pubblico, with the slender Torre del Mangia, stands at the bottom of the square, and inside are frescoes by Ambrogio Lorenzetti showing the effects of good and bad government, painted in the fourteenth century.
Siena was a rich republic and a rival of Florence, and its wealth came from banking and trade along the Via Francigena, the pilgrim road to Rome. The Monte dei Paschi, founded in 1472, is often described as the oldest surviving bank in the world. The city's cathedral, with its striped marble and an extraordinary inlaid floor, was intended to be even bigger, but the plague of 1348 put an end to the plans; the unfinished nave still stands. The historic centre is a World Heritage site.
Twice a year, on 2 July and 16 August, the Campo hosts the Palio, a bareback horse race between the city's contrade, or districts. It lasts about ninety seconds and is preceded by days of ritual, rivalry and celebration. If you are in Siena then, expect huge crowds and closed streets.
The centre is a limited traffic zone, a ZTL, and riding into it without permission brings automatic fines, so leave the bike outside the walls in one of the parking areas and walk. The riding around Siena is classic Tuscany: the SR2, the old Via Cassia, south toward the Val d'Orcia, and the roads through the Crete Senesi, a landscape of bare clay hills, offer gentle curves and huge views. To the north, the Chianti Classico roads toward Castellina and Radda are among the most popular biking roads in Italy.
Siena has fuel outside the walls and plenty of food. Try pici, a thick hand-rolled pasta, and panforte, a dense spiced cake. Spring and autumn are perfect for riding here.