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7 of the best towns and villages in Tuscany to visit in 2024

Simon Calder’s Travel

Although Italy has no shortage of enchanting holiday destinations – the Amalfi Coast, Cinque Terre, Puglia and Sicily, to name just a few – there’s something particularly magical about Tuscany.

This is a region that often seems to be bathed in a soft golden light, with gently sloping hills and beautiful Italian villas nestled among olive groves, cypress trees and vineyards.

Although you could easily fill your days in the cities of Florence and Pisa, or exploring the narrow streets and central piazza of Siena, perhaps one of the greatest experiences in Tuscany is exploring the many medieval hilltop towns and villages that are scattered through the countryside.

From famous towers of San Gimignano and charming Pienza to Greve in the wine-making region of Chianti, there are plenty of towns and villages to discover, all with their own unique charms and within easy driving distance of one another. Here are seven of our favourites.

San Gimignano

San Gimignano is famous for its 14 towers (Getty Images)

San Gimignano is one of the best known small towns in Tuscany – and for good reason. With its hilltop location, charmimg local restaurants and picture-perfect setting, it’s a favourite among tourists. Visitors can stroll through the medieval streets, stop in at one of the many small shops, gaze at the town’s impressive Duomo cathedral and visit the civic museum at the Palazzo del Popolo.

There’s a fun story behind San Gimignano’s famous towers. Between the 11th and the 13th centuries, the noble families who controlled the town believed their towers were a sign of wealth and power to their political and economic rivals, and so kept building more and more – it is believed that a total of 72 could be found in San Gimignano at its peak. Only 14 have survived, but they’re still rather impressive and give the town a palpable sense of history.

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The first written mentions of Montalcino date back to around 814 AD (Getty Images)

Montalcino is an excellent choice for wine lovers – it’s well known for its Brunello di Montalcino and Rosso di Montalcino wines. The location in the hills of the Val d’Orcia gives it an even more rustic setting than other towns on this list. Vistors will find themselves surrounded by countryside dotted with cypress trees and flowers, as well as rolling olive groves and…

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