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.

You could easily spend your days exploring Florence and Pisa, or wandering through the narrow streets and central piazza of Siena. But perhaps the greatest experience in Tuscany is discovering the many medieval hilltop towns scattered through the countryside.

From the 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.

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1. San Gimignano

San Gimignano is famous for its 14 towers (Getty)

San Gimignano is one of the best known small towns in Tuscany – and for good reason. With its hilltop location, charming 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 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.

Where to stay

Vegan Agrivilla I Pini, a pilgrim shelter turned vegan eco farmhouse, is a hotel with rustic rooms and a plant-based farm kitchen. Surrounded by rolling vineyards and olive groves, the hotel’s 11 lodgings are elegantly minimal to help you find your inner sanctuary.

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2. Montalcino

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

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. Visitors will find themselves surrounded by countryside dotted with cypress trees and flowers, as well as rolling olive groves and vineyards. Tourists can climb the fortress walls, amble through the winding streets and spend some time on the town’s Piazza del Popolo – but no visitor should miss the wine tastings which can be enjoyed in and around the town.

Where to stay

Perched just above the town, Borgo Canalicchio di Sopra Relais offers an authentic way to embrace the region’s speciality with copious opportunities to try the estate’s wines. After wine tastings, vineyard and cellar tours, cool off at the resort’s idyllic pools.

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3. Pienza

Pope Pius II originally commissioned a Florentine architect to transform his hometown of Corsignano into what is now Pienza (Getty)

Pienza also lies in the Val d’Orcia, where gently rolling hills are populated by Renaissance towns, vineyards and medieval castles. The town itself is surrounded by medieval walls, inside of which is a maze of pretty cobbled streets lined with typical Tuscan houses. From the town you can enjoy amazing views over the hills and olive groves, and in the distance sits Mount Amiata.

All roads in this town lead to the Pio II plaza, with particularly picturesque streets including the Via dell’Amore and Via del Bacio. The town’s cathedral sits in this square, as do Palazzo Piccolomini and Palazzo Borgia, which houses the town’s museum.

Where to stay

Just a stone’s throw from Pienza’s cathedral, history runs throughout the impressive Relais Il Chiostro Di Pienza. A former Franciscan convent, the hotel’s rooms are architecturally spectacular, completed with a garden terrace overlooking the Val d’Orcia.

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4. Greve in Chianti and Montefioralle

Greve in Chianti lies around 30km from Florence (Getty)

A visit to Tuscany is arguably not complete without a visit to Chianti, the region’s famous wine-producing area. Greve in Chianti is one of the more scenic towns in this part of Tuscany – it’s centred around the triangular Piazza Matteotti, the porticos of which hide vendors of various fresh produce.

In the foothills just below Greve in Chianti lies Montefioralle, one of the oldest villages in Tuscany. It’s still enclosed by its original defensive walls, and its (nearly) car-free centre is a great place for a relaxed stroll. The surrounding vineyards will likely be the focus of your visit, but be sure to climb up the hills to the highest point in the village where you can see the Santo Stefano church and take in a sweeping view of the vineyards, olive groves and cypress trees.

Where to stay

With bright furnishings and painted beams, each room in the luxury wine resort Borgo Del Cabreo is elegant and charming. Guests can enjoy homemade treats at breakfast before strolling to Greve in Chianti or booking an on-site cooking class to discover traditional Tuscan recipes.

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5. Volterra

This Tuscan town featured in part of the Twilight film series (Getty)

Volterra was once a mighty Etruscan city, but nowadays it is best known for Italian handicrafts and remnants of its medieval past. It is dominated by its Duomo along with the Palazzo dei Priori and 13th-century palazzo, though the 2,000-year-old Roman amphitheatre is another highlight. Remnants of its Etruscan past remain in the 5th-century Porta all’Arco walls and the Guarnacci Etruscan Museum, while the smaller Pinacoteca museum focuses on art from between the 14th and 17th century.

Where to stay

Just outside (15km) of the town itself, Borgo Pignano Volterra is perched on a hilltop with sweeping views across the Tuscan countryside. This 18th-century villa sits in 750 acres of countryside, with two pools (one of which is carved into the rock), an excellent restaurant focused on local produce and a range of activities, including horse riding around the estate, wine tasting (including the hotel’s own grapes), and artisanal workshops.

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6. Pitigliano

Pitigliano is considered one of the most beautiful villages of Italy (Getty/iStock)

Pitigliano is located in the Maremma region near the Tuscan coast. It’s another hilltop town, and features rows of sandstone buildings built on top of volcanic red “tuff” stone. As well as enjoying wine tastings, tourists can amble through the mazy streets, stop for a drink or bite to eat around the lovely Piazza del Popolo, explore the palace-fortress of Palazzo Orsini (and its museum) and visit the Sette Cannelle fountain.

This town is also known as “Little Jerusalem” as a large Jewish population resided there until around the time of the Second World War, and there are several remnants of its religious history still present, from an old Jewish Quarter – now with a Jewish museum – to a gilded synagogue.

Where to stay

Cross the ancient drawbridge to fairytale rooms and romantic courtyard at Hotel della Fortezza. Located in the neighbouring Sorano, the former 12th-century fortress offers a delightful way to explore both historic towns.

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7. Pietrasanta

Pietrasanta endured heavy fighting during the Second World War (Getty)

Pietrasanta still retains some of the artistic creativity that was associated with it in bygone times when artists such as Michelangelo frequented the town. Today it has one of the highest concentrations of art galleries in any Italian town, from the Favret MosaiciArtistici to the Flora Bigae gallery of contemporary art.

Pietrasanta is located very close to the coast, near upmarket resorts like Forte dei Marmi, and so is a town influenced by both local history and modern tourism. Away from the beaches, the highlights include the Duomo and the Rocca di Sala fortress, while an archaeological museum, marble quarry and yearly performing arts festival (La Versiliana) are a little more off the beaten track.

Where to stay

Overlooking a 100-year-old citrus grove, Orangerie prizes a central location and rooms finished with local antiques. Guests can wake up to breakfast under the orange trees, before stepping out to enjoy the town’s cultural delights.

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