The Most Beautiful Towns in Tuscany, Italy

Forget the Seven Hills of Rome – San Gimignano’s 15 towers are just as breathtaking. Less than an hour’s drive from Siena, this cascading commune was first raised by the ancient Etruscans, who came and clad the hills in slate and stone cottages. Following the fall of the Roman Empire, the Church took over, patronising the town with the glorious Sant’Agostino Basilica and the 12th-century Collegiate Church of Santa Maria Assunta. With this movement came a steady stream of pilgrims and poets who were quick to eulogise San Gimignano’s beauty and majestic surroundings of rolling cypress groves and saffron-hued fields.

Sandwiched between the Tyrrhenian Sea and the marble frontispieces of Pisa, Lucca clings like a limpet to the lowlands of the Serchio River basin. It’s entirely walkable and encircled on all sides by the best-preserved Renaissance bulwarks in all of Tuscany, which over centuries, has been claimed by the region’s ubiquitous cypresses and eucalyptus trees. In the heart of the town, the Piazza dell’Anfiteatro dominates with its ochre-painted stucco and sun-splashed al-fresco spaces – while the nearby Lucca Cathedral rarely fails to draw a gasp.

Draped over the hillsides of the pre-Apennines on the eastern fringes of Tuscany, Cortona is a stone-clad town topped with an imposing medieval tower. It’s a joy to wander through, thanks to the pretty, winding alleyways draped with washing lines and hanging baskets of roses and sage. Thanks to Cortona’s vantage point above the rolling plains of the Chiana Valley, sweeping panoramas of central Italy are available from almost every piazza – and Lake Trasimeno glimmers like a jewel in the distance. Marketplaces also erupt on the weekends, crammed between Garibaldi Square and the Cortona Cathedral in a medley of red wines and lampredotto sandwiches.

Montepulciano is primarily famed for its eponymous, full-bodied variety of red grape, as testified by the town’s many vineyards. However, 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; while the ancient streets ooze Etruscan history and Roman influence from each crack and crevice along the way.

If you prefer your wines fizzy then perhaps our Mini Trip in the Prosecco Hills of Veneto is your cup of bubbly.

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.

Cresting the hillsides of Massa and Carrara, Fosdinovo appears as a dash of brownstone and terracotta against the fir and olive forests of the Apuan Alps. At its heart stands the mighty and formidable outline of the Malaspina Castle of Fosdinovo, which has dominated the skyline since the 12th century. In the distance, the Tyrrhenian Sea marks the end of the Tuscan lands, while a cascade of stuccoed storeys and stone buildings clutch the rocks all around the ancient citadel. In essence, Fosdinovo is a town of pure drama and classic Italian charm.

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) – with 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, as 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 bougainvillaea, 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 where 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 1,870ft-long (570m) 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.

Clinging to the highland ridges of western Tuscany, the town of Volterra cloaks the old homeland of the Etruscans in a patchwork of medieval stone. Built and razed by the Romans, the grand Tuscan dukes and the formidable Medici family, the historic town plays host to ubiquitous basilicas, cobblestone streets, crumbling gateways and red-tiled roofs – while its sporadic piazzas bubble with the mellifluous tones of Italian chatter.