Perched on the green and leafy hills of central Tuscany, right on the cusp of the famous Val d’Orcia, Montalcino is quintessential Italy. It's surrounded by dashes of vineyard and neat rows of slender Mediterranean cypresses, eventually culminating with an old town that's awash with haunting medieval churches, walls, lookout points and keeps.

From the 1200s onwards, the town was a major trading outpost that specialized in leather and foodstuffs. These days, the ancient markets are gone, but Montalcino tour guides can still offer a glimpse of the rich history in the Diocesan Museum of Sacred Art, where whittlings and wood-panel paintings by Sienese masters abound. And that's just the start, because the whole center is a rabbit warren of stone steps, archways, hidden piazzas, and pretty chapels that hearkens back through the centuries. Just wander and get lost.

For the foodies, Montalcino is likely to be synonymous with wine. Like so many of the hilltop estates in this corner of the country, it's got its own famous tipple of rich red. You can sample that with Tuscan meat dishes and pastas in one of the myriad enotecas and trattorias.