The countryside around Siena is among the finest in Tuscany, and day trips in almost any direction are rewarding. The ruined Cistercian abbey of San Galgano — roofless and overgrown — is hauntingly beautiful. To the south, the Benedictine church of Sant'Antimo still functions as a monastery, with monks chanting Gregorian plainsong at dawn. Monte Oliveto Maggiore has a famous cloister frescoed by Luca Signorelli and Il Sodoma.
For hill towns, Monteriggioni is ringed by intact medieval walls; Montalcino produces Brunello, one of Italy's great wines; Montepulciano is a grand Renaissance town with commanding views; and Pienza, redesigned for Pope Pius II in the 15th century, is one of the most perfectly preserved Renaissance planned towns in Italy. The Chianti hills to the north — rolling vineyards, cypress avenues, stone farmhouses — are best explored by car or bicycle.