Tuscany renowned for its idyllic charm, from this historic architecture to the lush greenery landscape.
Captivating every kind of traveller to its picture-perfect region! 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 hillside.
Found in the southern side of Tuscany is the picturesque province of Arezzo. Cortona lies here, being a traditional walled Etruscan town, that sits on top of the highest point around. 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!
Sitting along the Serchio river, Lucca is one of the only Tuscan towns that isn’t nestled on a hilltop. Making a truly unique spot to visit in Tuscany, featuring stunning river views and renaissance 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!
This small town in Tuscany is found in the region of Maremma near the coast. Boasting tile-roofed buildings rest on the building’s red volcanic “tufa” stone, giving it’s 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 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. Due to all the town’s buildings being significant and historic, there hasn’t been a new building built since 1580, with each home and shop an important to the town. Step back in time and see the wondrous beauty in this small Tuscan charm as you try the local cuisines, sip the delicious wine, and be in awe of the history!
Related article: What is the best time of year to go to Tuscany?
Explore the Tuscany Tours
Tuscany Day Tour – Siena, San Gimignano, Pisa and Chianti Winery Lunch
See the best of Tuscany, including a wine tasting class and a delicious Tuscan style lunch.
1 Day Tuscany Bike Tour
Cycle your way through the Tuscan countryside, enjoying Tuscan style lunch and scenic wineries.
Morning Tuscany Vespa Tour from Florence
Venture to the Tuscan countryside, riding your own Vespa! Tuscan lunch & wine tastings included.
Pisa & Lucca Day Trip from Florence
Visit Pisa to marvel at its monuments and enjoy free time to explore medieval Lucca.