Exploring this reclaimed narrow ridge of volcanic rock will push your quadriceps to their failure point. When this happens, self-medicate with a generous pour of the highly reputed Vino Nobile while drinking in the spectacular views over the Val di Chiana and Val d'Orcia.
A late-Etruscan fort was the first in a series of settlements here. During the Middle Ages, the town was a constant bone of contention between Florence and Siena. Florence eventually won the day in 1404 and the Marzocco, or lion of Florence, came to replace the she-wolf of Siena as the city's symbol. The new administration invited architects including Michelozzo and Sangallo il Vecchio to design new buildings and endow this Gothic stronghold with some Renaissance grace and style. That intriguing mix alone makes the steep climbs worthwhile.