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Although Italy has no shortage of stunning holiday destinations— amalfi coastCinque Terre, Puglia and sicilyto name a few – there is something particularly magical about Tuscany.
This is a region often bathed in a soft golden light, with gentle mountains and beautiful scenery. italian villa Set among olive groves, cypress trees and vineyard.
You can easily spend a few days exploring Florence and Pisa, or wander Siena’s narrow streets and central squares. But perhaps the greatest experience in Tuscany is discovering the many medieval hilltop towns scattered across the countryside.
From the famous towers of San Gimignano and charming Pienza, to Greve in the Chianti wine region, there are many towns and villages to explore, all with their own unique charm and all within a short drive of each other. Here are seven of our favorites.
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Tuscany’s best towns and villages
1. San Gimignano
San Gimignano is one of the most famous towns in Tuscany, and for good reason. It’s a favorite with tourists thanks to its hilltop location, charming local restaurants and picturesque surroundings. Visitors can wander the medieval streets, stop at one of the many small shops, gaze at the town’s impressive cathedral, and visit the Civic Museum in the Palazzo del Popolo.
There is an interesting story behind San Gimignano’s famous tower. Between the 11th and 13th centuries, the noble families who controlled the town believed their towers were symbols of wealth and power over their political and economic opponents, and so continued to build more and more towers – at its peak, San Gimignano is believed to have had a total of 72 towers. Only 14 survive, but they are still impressive and give the town a palpable sense of history.
Where to stay
Vegan Agrivilla I Pini is a pilgrim sanctuary converted into a vegan eco-farmhouse, a hotel with rustic rooms and a plant-based farm kitchen. Surrounded by rolling vineyards and olive groves, the hotel’s 11 guest rooms are elegantly simple and help you find your inner sanctuary.
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2. Montalcino
Montalcino is a great choice for wine lovers – it’s famous for its Brunello di Montalcino and red di Montalcino wines. The location in the hills of Val d’Orcia gives it a 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. Visitors can climb the fortress walls, stroll through the winding streets and spend some time in the town’s Piazza del Popolo, but no visitor should miss a wine tasting in and around the town.
Where to stay
Borgo Canalicchio di Sopra Relais is situated above the town and offers numerous opportunities to taste the estate’s wines and experience the region’s gastronomic specialties in an authentic way. After wine tasting and tours of the vineyards and cellar doors, cool off in the resort’s idyllic pool.
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3. Pienza
Pienza is also located in the Orcia Valley, where the rolling hills are dotted with Renaissance towns, vineyards and medieval castles. The town itself is surrounded by medieval walls, and within the walls is a labyrinth of pretty cobbled streets lined with typical Tuscan houses. From the town you can enjoy stunning views of the hills and olive groves, with Mount Amiata in the distance.
All roads in the town lead to Pio II Square, which has picturesque streets, including Via dell’Amore and Via del Bacio. The town’s cathedral is located in this square, as are Palazzo Piccolomini and Palazzo Borgia, which serves as the town’s museum.
Where to stay
Just a stone’s throw from Pienza Cathedral, the impressive Relais Il Chiostro Di Pienza is steeped in history. The hotel is a former Franciscan convent and its architecturally beautiful rooms have garden terraces overlooking the Val d’Orcia.
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4. Greve and Montefiorale in Chianti
No trip to Tuscany would be complete without a visit to the region’s famous wine region, Chianti. Greve in Chianti is one of the most picturesque towns in this part of Tuscany, centered around the triangular Piazza Matteotti, whose porticoes hide vendors of all kinds of fresh produce.
Situated in the foothills below Greve in Chianti, Montefioralle is one of the oldest villages in Tuscany. It’s still surrounded by the original defensive walls, and its (almost) car-free center is a great place for a relaxing stroll. The surrounding vineyards may be the highlight of your visit, but be sure to climb up the hill to the highest point in the village, where you can see the church of Santo Stefano and take in sweeping views of the vineyards, olive groves and cypress trees.
Where to stay
Each room at the Borgo Del Cabreo luxury wine resort is elegant and charming, with bright furnishings and painted beams. Guests can enjoy homemade delights 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
Volterra was once a powerful Etruscan city, but today it is famous for its Italian artefacts and medieval ruins. The city is dominated by its cathedral, Palazzo dei Priori and 13th-century palaces, but the 2,000-year-old Roman amphitheater is another highlight. The 5th-century Porta Alco walls and the Etruscan Museum of Guanachi preserve remnants of Etruscan history, while the smaller Pinacoteca Museum focuses on art from the 14th to 17th centuries.
Where to stay
Borgo Pignano Volterra is just outside the town (15 km), perched on a hilltop with unobstructed views of the Tuscan countryside. Set in 750 acres of countryside, this 18th-century villa has two swimming pools (one of which is carved into the rock), an excellent restaurant focusing on local produce, and a range of activities including horse riding around the estate, wine tastings (including the hotel’s own grapes) and craft workshops.
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6. Pitigliano
Pitigliano is located in the Maremma region near the Tuscan coast. This is another hilltop town that features rows of sandstone buildings built on red volcanic “tuff” stone. In addition to enjoying wine tastings, visitors can stroll through the maze of streets, stop for a drink or a bite to eat around the lovely Piazza del Popolo, explore the palatial fortress (and its museum) of Palazzo Orsini, and visit the Setcanelle Fountain.
The town is also known as “Little Jerusalem” because a large number of Jews lived there until the Second World War, and some vestiges of its religious past remain, from the ancient Jewish Quarter (now home to the Jewish Museum) to the gilded synagogue.
Where to stay
Cross the ancient suspension bridge to the fairy-tale rooms and romantic courtyard of Hotel de la Fortezza. This former 12th-century fortress is located in neighboring Sorano, providing an enjoyable way to explore these two historic towns.
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7. Pietrasanta
Pietrasanta still retains some of the artistic creativity of bygone eras, 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 contemporary art gallery.
Pietrasanta is very close to the coast and close to upscale resorts such as Forte dei Marmi, so it is a town deeply influenced by local history and modern tourism. Highlights away from the beach include the cathedral and Rocca di Sara fortress, while the archaeological museum, marble quarries and the annual performing arts festival (La Versiliana) are slightly more secluded.
Where to stay
Overlooking a 100-year-old citrus grove, the Orangerie has a central location and rooms furnished with local antiques. Guests can wake up and have breakfast under the orange trees before heading out to enjoy the cultural delights of the town.
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