Delightful towns in the Tuscan hills
Mini guide to 10 lesser-known hill towns in Tuscany

Want to discover those lesser-known parts of Tuscany's beautiful rolling hills? Here are 10 beautiful and unknown hilltop towns, some of Tuscany's best vacation spots to explore for a day (or even for a longer stay). With the selection at hand, it's not easy to choose only 10: Tuscany is filled with charming towns to explore, as almost 70% of its hills are dotted with delightful villages.

Here are a few beautiful destinations to consider:


Barga is one of the most recognized medieval villages in Tuscany for its historical, artistic and tourism-related significance. It is nestled in the heart of the Serchio river valley and is the chief town of Lucca’s media valle (mid-valley). Its charming location, nestled between the Tuscan-Apennine hills and the majestic Apuan Alps separating Garfagnana and Versilia, make it all the more beautiful. A medieval castle and city wall dominate the town, which can be accessed via three main gates. The town has remained virtually unchanged throughout time, with narrow streets weaving between oddly shaped buildings. In piazza Ser Barghesano you’ll find a Romanesque cathedral built between the 11th and 16th centuries. Check out what else you can see and do in Barga.


Inhabited since the Paleolithic era and nestled in the Montalbano hills (only 10 km from Prato), the town of Carmignano merits a visit not only for its stunning landscape but also for its food and wine products (you’ll even find the Museum of Vine and Wine!). Don’t miss the well-preserved 10th-century fortress in the upper part of town, the 12th-century Church of San Michele e Francesco housing Pontormo’s Renaissance masterpiece, the Visitation, a number of Etruscan tombs in Comeana and the beautiful Medicean Villa in Artimino. Check out how to plan a trip to Carmignano.

Casale Marittimo

Casale Marittimo is located on the “wine route” along the Etruscan Coast, near Cecina. This little gem dates to the year 1000, and hasn’t changed much since then. You’ll find stone buildings, a castle, two concentric circular walls and other age-old marvels: a clock tower, the Casa del Camarlingo, the Palazzo della Canonica (in front of the Church of Sant’Andrea) and the small Church of San Sebastiano dating to 1775. Casale Marittimo is also home to a grave dating to the 5th century B.C.E. and a Roman Imperial villa. Check out, Casale Marittimo on the Wine Route.

Casole d’Elsa

Casole d’Elsa is a picturesque medieval village located in the Val d’Elsa, located 417 m high and about 25 km west of Siena. For centuries the Etruscan-inhabited Casole and its surrounding areas were cause of battle for Sienese, Florentine and Volterran forces. Today, you can visit its many important buildings, such as the Romanesque Church of San Niccolò, the Collegiate Church of Santa Maria Assunta dating to 1161, the Church of Santo Spirito and even Palazzo Pretorio, the centuries-old seat of the town council.


Cetona is a village located on the northeastern slopes of its namesake mountain, inhabited by humans since prehistoric times. The town of Cetona is located on the hillside surrounding the fortress, vaunting a square tower and an inner fortress wall. The collegiate church, the Church of San Michele Arcangelo and the Town Hall are all worth a visit. Don't miss the archaeological finds on display in the Civic Museum of the Prehistory of Mount Cetona and the Belverde Archeological - Natural Park, not to mention the town's high quality of life and pristine environment. To this end, Cetona is considered a striking destination for its typically medieval layout and thick vegetation, which set the tone for a relaxing holiday. Here are 3 more reasons to visit Cetona.


Cutigliano is a medieval town that rises 678 m above sea level in the Tuscan-Emilian Apennines (near Pistoia). As with many other Tuscan towns on this list, it was awarded the “Orange Flag” label for its welcoming atmosphere and beautiful setting. Among the town’s main sights, don’t miss the golden-hued town hall vaunting numerous coats of arms and the Church of the Madonna di Piazza, which dates to 1600 and houses a precious Della Robbia-style terracotta panel. For more about Cutigliano, click here.


Fosdinovo is a hilltop town overlooking the sea only 15 km from Massa, considered a real gateway to the Lunigiana. The town is home to the medieval-era castle of the Malaspina family, found in the town center. While wandering through the narrow streets you'll also see the Church of San Remigio, the theater and the Oratorio della Compagnia. From the top of Fosdinovo you can enjoy views of the Magra river valley, Portovenere and Palmaria, and on clear days, even the islands of Capraia, Gorgona, Elba and Corsica. Read more about Fosdinovo, a medieval hamlet in Lunigiana.

Giglio Castello

Giglio Castello is located in the central part of Giglio Island between Giglio Campese and Giglio Porto. This ancient medieval town still boasts its original look: imposing fortress walls and sky-high watchtowers decorate the town, while three granite doorways mark its main entrance. Once inside, stroll along the town’s walkways or through its narrow streets lined with stairs and terraces. Arches, dark underground passages, steep steps carved into rock and age-old houses make Giglio Castello one of a kind. Check out more ideas for an unforgettable stay on Giglio island.


Only 6 km from Manciano you’ll find Montemerano, a 12th-century town in the heart of the Maremma. This hilltop town was built by the powerful Aldobrandeschi family and is completely enclosed by fortified walls. Three city gates serve as entranceways to the town’s maze of narrow streets. Inside, head to the 14th-century Church of San Giorgio, the town’s main parish church, and the 12th-century Parish Church of San Lorenzo, the oldest building in Montemerano. Check out Montemerano, a hidden gem in the Maremma.

Radda in Chianti

Immersed in the incomparable beauty of the Chianti region, located between the Arbia and Pesa valleys, you'll find the enchanting town of Radda in Chianti (530 m above sea level). Radda in Chianti is a delightful medieval town enclosed by large defensive walls still vaunting their medieval look. Narrow streets converge in the main square where the Romanesque Church of San Niccolò proudly dominates the village. Don’t miss the Grand Duke’s Ice House or the Museum of Sacred Art of Chianti located in the Franciscan Convent of Santa Maria in Prato. Wherever you decide to go, don’t miss savoring a glass of Chianti Classico DOC produced in the area.