The 10 Most Beautiful Towns in Tuscany

Montepulciano is primarily famed for its eponymous, full-bodied variety of red grape, as testified by the town’s many vineyards. But rustic Tuscan beauty is also why so many choose to visit this red-brick and terracotta municipality on the ridges of the Val d’Orcia every year. Tight-knit lanes weave their way up to the centre, where the Piazza Grande shines with marble and travertine masterpieces. Here you’ll find the Palazzo Comunale and the Palazzo Nobili-Tarugi, with their chiselled columns and shadowy archways. Nearby, slanting tiled roofs flow like a river down into the pine and cypress woods below; the ancient streets ooze Etruscan history and Roman influence from each crack and crevice along the way.

Set just back from the refreshing rollers of the Mediterranean, Suvereto continues to reign as one of Tuscany’s most handsome little towns. It’s located between the forests of Livorno Province, which roll out westward into the rugged hills of Campiglia Marittima and eastward toward the pastures and olive groves of the Marsiliana Reserve. Travertine and rough-hewn stone buildings dominate the town’s centre, crowned by an early-Renaissance castle covered in creeping vines and spotted with lichen. In the middle of it all runs Via Matteotti, a street populated by slow-food gourmet joints, cellar doors and fascinating porticos from beginning to end.

In the shadow of the great Pania della Croce, Barga pokes above the Tuscan highlands. The town’s mighty duomo and the yellow and beige faces of its old Renaissance manors are set in stark contrast to the alpine hills behind. Rustic beauty flows through the streets and piazzas, while a curious Scottish character is also palpable in the town’s annual Sagra del Pesce e Patate (Fish and Chips Festival) and the anachronistic red telephone boxes peppering the corners.

Pitigliano rises vertically from its own sheer-cut bluff in the middle of the borderlands between Tuscany and Lazio. It stands firm and tall like some kind of organic extension from the tufa rock bowls below – chiselled out from the monolith by the Etruscans, dusted off by the Romans and crowned with the wealth of the Orsini family. In the centre, up top, winding cobblestone streets dip and duck under archways and cascades of bougainvillea, while shadowy stairways lead to the front of enchanting synagogues (a famous feature of this town). Time your visit to coincide with one of the traditional festivals that erupt on the Piazza Garibaldi.

To pass under the concentric walls of Monteriggioni is to journey back in time to when the two great Tuscan forces, Siena and Florence, were battling for control of the region’s heart. As a testimony to its place on the front line of contact between these two historic city states, the entire town centre is encased in a 600m-long (1,969ft) bulwark of stone. Built in the 13th century, the wall still marks the boundary between Monteriggioni’s inner sanctum of sun-splashed piazzas and flowery trattoria gardens, and the olive-dotted hinterland of central Tuscany outside.