What is the prettiest town in Tuscany?

Tuscany renowned for its idyllic charm, from this historic architecture to the lush green landscape.

Tuscany captivates every kind of traveller with its picture-perfect scenery! However, with so many towns to choose from, Tuscany’s many pretty locations can be hard to pick! Luckily, we’ve researched for you, listing the top prettiest towns in Tuscany for a truly unforgettable adventure around the countryside.

• Cortona

  Found in the southern side of Tuscany is the picturesque province of Arezzo. Cortona, a traditional walled Etruscan town, sits here on top of the highest point, offering spectacular views over the surrounding valley and Lake Trasimeno. It may be on the smaller size, but there is plenty to see when visiting this historic region, from famous panel paintings, fascinating artefacts, and even a couple archaeological sites!

• Lucca

  Sitting along the Serchio river, Lucca is one of the only Tuscan towns that isn’t nestled on a hilltop. A truly unique spot to visit in Tuscany, Lucca features stunning river views and treelined town walls. The streets all connect, slowing winding into the very centre of the town, known as Piazza dell’Anfiteatro. Being the heart of Lucca, the centre is lined with endless shops, bars, and restaurants, bustling with both tourists and locals going about their day!

• Pitigliano

  This small town in Tuscany is found in the region of Maremma near the coast. The tile-roofed buildings resting on the building’s red volcanic “tufa” stone give Pitigliano a truly unique look. The beauty of the region isn’t just the design, but the history attached, with the town nicknamed ‘the Little Jerusalem’, named from the town’s Jewish history. Make sure to visit the underground tunnels and caves dug beneath the city, with this labyrinth of passages and rooms truly an unforgettable sight to see!

• Montepulciano

  Montepulciano is a smorgasbord for the senses. Renaissance art covers this medieval town, with the affluent Medici family in the 16th century bringing a large amount of architecture and artwork into the region. All the town’s buildings are significant and historic and there hasn’t been a new building built since 1580. Step back in time and see the wondrous beauty in this small Tuscan charmer as you try the local cuisines, sip the delicious wine, and be in awe of the history!

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