San Gimignano
Forget the Seven Hills of Rome, San Gimignano’s 15 towers are just as handsome and breathtaking. Spiking the Tuscan sky and under an hour’s drive north-west of pretty, red-brick Siena, this cascading commune was first raised by the ancient Etruscans, who came and clad the undulating 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, while bringing with them 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.
Lucca
Sandwiched between the wide coastal stretches that run their way along the edge of the Tyrrhenian Sea and the marble-clad frontispieces of Pisa just to the south, Lucca clings like a limpet to the verdant lowlands of the Serchio River basin. It’s encircled on all sides by the best-preserved Renaissance bulwarks in all of Tuscany, which have become moss-clad and claimed by the ubiquitous cypresses and eucalyptus trees over the centuries. It is topped with parkland and is entirely walkable. In the heart of the town, the elliptical 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.
Cortona
Draped over the rising hillsides of the pre-Apennines on the extreme eastern fringes of Tuscany, Cortona is a stone-clad town topped with one gorgeous medieval tower, and littered with winding alleyways where swinging washing lines give way to blooming hanging baskets of rose flowers and sage. Thanks to its high-perched position over the rolling plains of the Valdichiana below, sweeping panoramas of central Italy are available from most all of the flagstone-covered piazzas; the shimmering waters of Lake Trasimeno glimmering like a jewel between the rugged valleys in the distance. Marketplaces also erupt ad hoc on the weekends, crammed between Garibaldi Square and the Santa Maria Cathedral in a medley of red wines and lampredotto sandwiches.
Montepulciano
Montepulciano is primarily famed for its eponymous, full-bodied variety of red grape, as testified by the town’s endless vineyards. But rustic Tuscan beauty is also why so many visitors choose to head to this red-brick and terracotta municipality on the ridges of the Val’dOrcia 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 enfolding chiselled columns and shadowy archways. Nearby, slanting tiled roofs flow like a river down into the pine and cypress woods below; the ancient streets oozing Etruscan history and Roman influence from each crack and crevice along the way.
Suvereto
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 nestled between the cork and cypress-dotted forests of Livorno Province, which roll out westwards into the rugged hills of Campiglia Marittima and eastwards towards the verdant greenery of the Marsiliana Reserve. Travertine and rough-hewn stone buildings dominate its centre, crowned by an early-Renaissance castle that now stands in creeping vines and spotted with lichen above the slim alleyways of the old town below. In the middle of it all runs bustling Via Matteotti, threaded with slow food gourmet joints, cellar doors and fascinating porticos from beginning to end.
Fosdinovo
Cresting the hillsides of Massa and Carrara, Fosdinovo appears as a dash of brown stone 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. Fosdinovo is a town of pure drama and Italian charm.
Barga
In the shadow of the snow-topped, mist-mantled mountain summits of the great Pania della Croce, Barga pokes above the Tuscan highlands, between the sweeping greenery of chestnut forests and olive trees that dominate all around. Its mighty duomo and the yellow, lemon and beige-coloured faces of its old Renaissance manors set in stark contrast to the icy alpine hills behind. Awarded the prestigious Orange Flag by the Italian Touring Club, rustic beauty flows through the close-knit 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
A phalanx of stone and brick that rises vertically from its own sheer-cut bluff in the middle of the borderlands between Tuscany and Lazio, Pitigliano is the stuff of travel brochures and postcards. 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 swoop low, shadowy stairways lead to the front of enchanting synagogues (a famous feature of this town), and traditional festivals erupt on the Piazza Garibaldi.
Monteriggioni
To pass under the concentric walls of Monteriggioni is to journey back in time, back to when the two great Tuscan forces, Siena and Florence, were battling for control of the region’s heart. Testimony to its place right on the front line of contact between these two historic city states, the entire town centre is encased in a 600-meter-long bulwark of stone. Built in the 13th century, the wall still marks the boundary between Monteriggioni’s inner sanctum of sun-splashed piazzas and flower-clad trattoria gardens and the olive-dotted hinterland of central Tuscany outside.
Volterra
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, its historic centre 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.
