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Exploring the medieval town of Montepulciano, perched on a reclaimed narrow ridge of volcanic rock, will push your quadriceps to failure point. When this happens, self-medicate with a generous pour of the highly reputed Vino Nobile while also drinking in the spectacular views over the Val di Chiana and Val d'Orcia.
These are our favorite local haunts, touristy spots, and hidden gems throughout Montepulciano.
Street
Montepulciano's main street – called in stages Via di Gracciano, Via di Voltaia, Via dell'Opio and Via Poliziano – climbs up the eastern ridge of the town from Porta al Prato and loops to meet Via di Collazzi on the western ridge. To reach the centre of town (Piazza Grande), take a dog-leg turn into Via del Teatro.
Palace
Built for Cardinal Giovanni Maria Ricci in the 16th century, this handsome palazzo has a rear loggia with a stunning view of the countryside. Home to many generations of the Ricci family over the centuries, it's now owned by the municipality and hosts the the European Academy for Music and Performing Arts and Cantina de' Ricci, a cavernous warren of ancient wine cellars.
Museum
It was a curatorial dream come true: in 2011 a painting in the collection of this modest art gallery was attributed to Caravaggio. The work, Portrait of a Man, is thought to portray Cardinal Scipione Borghese, the artist's patron. It’s now accompanied by a touch-screen interpretation that allows you to explore details of the painting, its restoration and diagnostic attribution. Other works here include two terracottas by Andrea Della Robbia, and Domenico Beccafumi's painting of the town's patron saint, Agnese.
Piazza
Elegant Piazza Grande is the town's highest point and main meeting place. If you think it looks familiar, it might be because it featured in New Moon, the second movie in the Twilight series based on Stephenie Meyer's vampire novels. They shot the main crowd scene here, despite the book being set in Volterra. More recently, it features in episodes of the television series Medici: Masters of Florence.
Cathedral
Montepulciano's 16th-century duomo is striking, largely because its unfinished facade gives the building a stern, heavily weathered look. Inside, don't miss Taddeo di Bartolo's ornate Assumption triptych (1401) behind the high altar and Sano di Pietro's Madonna del pilastro (Madonna of the Pillar; 15th century) on the eastern wall of the nave.
Church
Designed by Antonio da Sangallo (Sangallo il Vecchio) and constructed in the late-16th century, this splendid Renaissance church in the valley below the upper town has a distinctive central dome and pyramid-topped bell tower. The church is dedicated to San Biagio (St Blaise), the Armenian-born martyred patron saint of wool combers.
Street
From the central Piazza Grande, Via Ricci runs downhill past Palazzo Ricci, now home to the European Academy for Music and Performing Arts. The street terminates in Piazza San Francesco, where you can admire more panoramic views of the Val di Chiana.
Palace
Built in the 14th century in Gothic style and remodelled in the 15th century by Michelozzo, the Palazzo Comunale still functions as Montepulciano's town hall. Head up the 67 narrow stairs to the tower to enjoy extraordinary views – you'll see as far as Pienza, Montalcino and even, on a clear day, Siena.
Monument
At the upper end of Piazza Savonarola is the Colonna del Marzocca, erected in 1511 to confirm Montepulciano's allegiance to Florence. The stone lion atop this column is, in fact, a copy; the original is in the town's Museo Civico.