The 10 Most Beautiful Towns in Tuscany

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.

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.

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.

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.

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.

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.

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.

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.