Published 28th Jun. 2024
Written by Emily Dundas
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There are some destinations that pull on your heartstrings, and Tuscany is most certainly one of them. Picture lovely landscapes dotted with cypress trees, olives groves and rolling wheat fields; Medieval villages perched high up in the hills; and shady trellises that act as the perfect spot to sit back, relax and soak up the views in Italy. Our experienced consultants have put together their guide to the most beautiful villages in Tuscany, so you can experience the region in all its glory...
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For travellers looking to learn about Tuscany’s history, Volterra is a must visit. Located in the heart of the region and perched prettily on a hilltop overlooking the Cecina and Era valleys, it's the perfect place to gain an insight into the region's rich heritage (it helps that this walled town is also one of Tuscany’s most beautiful). From the Etruscan tombs dating back several centuries BC, to the medieval churches and 16th-century palaces, Volterra tells the story of this region and the lengthy battle Florence and Siena fought to control it.
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Another ancient Etruscan city, Arezzo was once a rival to neighbouring Florence and Siena (and you’ll understand why once you start exploring). Head to the Basilica of San Francesco to see the famous and beautifully restored frescoes by Piero della Francesca, a hugely admired Renaissance artist. After taking a stroll past the beautiful Romanesque church of Santa Maria della Pieve, make sure to order a hearty bowl of the famous ribollita (an ancient Tuscan vegetable soup), before paying a visit to the Casa Vasari and Casa del Petrarca house museums.
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Sitting on the border of Tuscany and Umbria, north of Lake Trasimeno, Cortona was once an important Etruscan city. Proof of this can still be seen today in the enormous walls that hug the city, as well as in the inscribed bronze Tabula Cortonensis which is on display at the town's Etruscan Academy Museum. Steeped in Tuscan charm, Cortona is home to an impressive collection of religious art, including works such as 'Virgin with Child' by Pietro Lorenzetti, 'Annunciation' by Fra Angelico and 'Pieta' by Pietro da Cortona. Venture outside the walls and find the church of Santa Maria Nuova, built in the mid-16th century by Italian architect Giorgio Vasari who was famous for first using the term 'Renaissance'. Cortona is also perfectly located, with Siena, Arezzo, Perugia and Assisi all within an hour's drive of the town, making this area ideal for road tripping around Tuscany’s most beautiful towns and villages.
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San Gimignano's historic centre is a UNESCO World Heritage site, and – in our opinion – one of the most beautifully preserved towns from the 13th and 14th centuries. Its characteristic Medieval towers, silhouetted against the town's skyline, are an impressive sight. Dating even further back is the Collegiate Church of Santa Maria Assunta, on the Piazza del Duomo. Inside the church there are several must-see frescoes, including the 'Last Judgement' by Taddeo di Bartolo and 'Stories from the New Testament' by Lippo and Federico Memmi. Don't miss a visit to the Palazzo del Popolo, either. This town hall, where Dante once spoke, is home to yet more amazing artwork, and with so much to offer, even hard-to-please children will be won over by San Gimignano's old-world, artistic charms.
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The charming village of Montepulciano, situated in the province of Siena, was founded over 1,500 years ago and is without doubt one of the most beautiful villages in Tuscany. The wine produced in this area is pretty special too, making Montepulciano a must for oenophiles. Stroll along the narrow streets until you reach the main square at Piazza Grande, and then on to the San Biagio church to soak up some picture-perfect panoramic views of the Tuscan countryside.
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This lovely Tuscan village, situated between Montalcino and Montepulciano, offers sweeping views of the surrounding landscape. Pienza is another UNESCO World Heritage site and also happens to be the birthplace of Pope Pius XII who was head of the Catholic Church from 1939 until his death in 1958. Take a stroll along its ramparts and narrow streets, admiring gorgeous scenes over the hills of Val d'Orcia.
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The fortified town of Montalcino sits on a hilltop overlooking the rolling hills of Val d'Orcia. Spend an afternoon navigating the Old Town's charming narrow streets then head into the nearest wine bar and grab a glass of Brunello di Montalcino, the delicious red wine produced in the region. This Medieval city is a treasure trove of cultural and historical attractions, including a mighty fortress, picturesque churches and the Abbey of Sant'Antimo, which is just a few miles south.
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Pitigliano, located in the south of Tuscany, is an ancient Medieval town perched dramatically on a limestone cliff. Throughout history it’s been referred to as ‘Little Jerusalem’ in reference to the Jewish community that has been settled there since the 15th century and today you can visit the Museum of Jewish Culture and the oven where unleavened bread was once baked. What makes this one of the most beautiful towns in Tuscany is its narrow sloping streets connected by covered passageways which are perfect for shady afternoon strolls.
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The Medieval town of San Quirico d'Orcia, located halfway between Siena and Orvieto in the Orcia valley, is as pretty as a postcard. The town is surrounded by ramparts and dotted with impressive gateways and the surrounding landscapes are quintessential Tuscany (think: winding roads lined by cypress trees, rolling green hills and handsome historic architecture).
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Monteriggioni is a fortified village in the heart of rural Tuscany which was used as inspiration for the video game 'Assassin's Creed'. With its two main streets, a cobbled square dominated by a Romanesque church and a tiny museum dedicated to the Knights Templar, it's the perfect place to round off our list of the most beautiful villages in Tuscany.
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