Forget the usual tourist trail of Florence, Siena and Pisa, because Tuscany has more up its sleeve than just leaning towers and the Ponte Vecchio. Laden with rustic villages, ancient Etruscan settlements, and enthralling mazes of stone and marble, this region has to be one of the most beautiful in all of Italy. From San Gimignano to Volterra, here are 10 of the most beautiful towns to visit in Tuscany – and an Airbnb recommendation for each.
Forget the Seven Hills of Rome – San Gimignano’s 15 towers are just as handsome and 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, 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.
Immerse yourself in the gripping history of San Gimignano with a stay at this Airbnb, housed in a tower that dates back to the 12th century, in the heart of the town. Sleeping three guests over two bedrooms, it comes with panoramic views of San Gimignano from the tower’s rooftop.
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 have 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.
With its sunny terracotta-coloured exterior and gorgeous outdoor patio, this four-guest townhouse is made for al-fresco afternoons. The inside is just as spritely, stylishly decorated and well equipped. A fully stocked kitchen means you can easily whip up a meal here during your stay.
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 ad hoc on the weekends, crammed between Garibaldi Square and the Santa Maria Cathedral in a medley of red wines and lampredotto sandwiches.
Housed just outside the centre of Cortona, this cottage is a charming base for your time in Cortona. From the front door, the views stretch over the surrounding countryside and vineyards to Lake Trasimeno. Sleeping just two people, the cottage is a romantic, rural bolt-hole.
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.
This enormous house – sleeping 10 guests over three bedrooms – feels quintessentially Tuscan the minute you step inside. Terracotta tiles abound on the floors, and wooden beams add structure and intrigue to the ceilings. The Jacuzzi and sauna are also a delightful way to unwind after a day walking around this fairytale town.
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.
A house fit for royalty, this show-stopping seaside villa sleeps 13 guests over five bedrooms. The enormous beachfront terrace allows you to make the most of the spectacular location, while the indoor pool is perfect for cooling off.
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.
Live out all your royal dreams in this historical castle, sitting atop a hill on the outskirts of Fosdinovo. Sleeping 14 guests over seven bedrooms, the place is an architecture buff’s dream, with elements from the 12th, 16th and 19th centuries.
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.
Sleeping four guests, this apartment comes with an enormous terrace that offers wonderful views of the sorbet-coloured houses of Barga. You can spend your evenings sipping locally made wine and dining on fresh produce while incredible vistas surround you.
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.
Located in the heart of Pitigliano, this attic flat sleeps five guests and comes with striking views of the town. Two terraces give panoramic vistas of the terracotta rooftops and sandstone buildings below, and host Marella is on hand for any help you need.
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.
Fancy sleeping inside the castle walls of Monteriggioni? A stay in this Airbnb places you right at the heart of a slice of medieval history. Surrounded by traditional bars and restaurants, this place offers no shortage of opportunities to lift the lid on life in Monteriggioni.
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.
Seamlessly fusing the old and the new, this two-bedroom apartment sleeps four. While the space has a slick and modern feel, it has retained some of its historical features – including exposed stone walls and striking brick ceilings.
