Some of the most charming attractions in beautiful Tuscany are its numerous hilltop towns, dating back centuries. While many are a standard part of Tuscan tour itineraries, others remain relatively unknown. That is part of their charm for visitors who are looking for unspoiled hill towns that aren’t overrun with tourists.

Three of the most interesting but undiscovered hill towns are Anghiari, Collodi, and Trequanda. They each offer unique attractions and a welcoming atmosphere for visitors.


Anghiari: Historic Battles and Artistic Masterpieces

Perched on a hill in the countryside of Arezzo, Anghiari is a small, medieval town with beautiful views and a rich history. It lies near the border between Tuscany and Umbria in the lush Valtiberina Valley. The walled town has characteristically narrow streets and stone cottages, dotted with flowers in bloom on balconies.

The earliest known references to the town date its existence to 1048. Built up from the flat valley on a hill constructed of stones and surrounded by massive walls, Anghiari held a critical strategic position during the Middle Ages. Its location was positioned on trade routes that linked the central part of Italy with the Adriatic Sea. And its well-protected, lofty setting made it strong in war.

The town is most known for the Battle of Anghiari, between Florentine and Milanese armies, which took place in 1440. The fame of the battle is due less to its historical significance and more to its depiction in one of Leonardo de Vinci’s art masterpieces. This Renaissance fresco, Battle of Anghiari, is now lost to history. After the artist created full-scale drawings, he began to transfer them onto the walls as a fresco and completed a central section. However, the painting became damaged as it dried, and the uncompleted fresco decayed. Substitute frescos by another artist eventually were painted over it. Art historians have decried this loss, as it was considered a dazzling innovative work in its day. Luckily, many other artists came to view it during its creation and to make copies. Versions by Rubens and Biagio di Antonio live on in museums today.

In addition to this artistic quirk of history, Anghiari is worth a visit for its preservation of its history in a charming natural setting. Views from the town are panoramic, overlooking the Upper Tiber and Sovara valleys. The town itself is quite well preserved, with most of its city walls remaining intact, including three gateways. Several prominent eighteenth-century buildings are also preserved, including the Palace that now houses a theatre, library, and other enterprises. Several museums record the cultural and historical history of Anghiari, with exhibits that include medieval sculptural fragments, ancient firearms, medieval manuscripts, and prehistoric tools.

If you visit Anghiari, take in the museums, by all means. But leave plenty of time for long strolls through the streets, where you can feel the pull of centuries of art, architecture, and Tuscan history.

Collodi: Land of Fairy Tales and Gardens

The small hill town of Collodi, which lies east of Lucca, is best known as the birthplace of the mother of Italy’s most famous children’s author. Carlo Lorenzini used the pen name of Collodi to write Pinocchio, a fairy tale that gained international fame when it was adapted for the screen by Walt Disney. A large park, Parco di Pinocchio, dedicated to the world’s most famous puppet, now graces the town.

While one might expect a Disney theme park adventure here, the park is surprising in its charm and craftsmanship. When it was commissioned, artists were invited to submit their recommendations for the proposed park, and competitions were held for artwork to be featured in the park. The park features a group of remarkable sculptures designed by Emilio Greco. Bronze statues depict characters from the original fairy tale, as well as trace the evolution of Pinocchio from marionette to little boy. Many of the statues have water features, and each features a quotation from the children’s tale. A square decorated in Italian mosaics depicts episodes in the story, while the statues lie along a wooded trail. Even visitors without children should enjoy this beautifully depicted return to childhood, if just for an afternoon.

The other main attraction of Collodi is Villa Garganozi, an impressive home and gardens directly across from Pinocchio Park. The 17th century villa is most notable for a spectacular cascading garden that covers the sloped land surrounding the villa. It contains both Renaissance and Baroque design elements, as well as the last remaining garden labyrinth in the Lucca area. Numerous grottoes, fountains, and statues dot its landscape. The villa itself is currently closed for restoration, but it is a striking sight, perched on the hillside’s steep slope. It was built by the family who owned the town dating from the 14th century.

The Villa Garganozi is part of what is called Old Collodi, to distinguish it from the more modern development associated with Parco di Pinocchio. Old Collodi appears to throw itself down a wooded hill in a jumble of old cottages and cobblestone streets, bordered by groves of olive trees. The medieval patina of the old village is punctuated by the bright colors of terracotta roofs and vivid geraniums. Ancient communal wash tubs sit in a town square, and an old fortress and 13th century church also capture the town’s history through the centuries.

Whether you are drawn to medieval history and terraced gardens or a poignant children’s story, you’ll find that charming Collodi has something worthwhile to offer you.

Trequanda: Off the Map

Located in the province of Siena, this small town of approximately 2200 is so undiscovered that it does not even appear on most maps of Tuscany. It is a fortified village that dates back at least to medieval times, although there is evidence that it may have actually originated in the Etruscan era. Today the small town is primarily an agricultural community, but it is soaked in the history of the Middle Ages.

Buildings dating back as many as 600 years face the town’s central square, the Piazza B. Cacciaconti. As in any classic hill town, the piazza is the focus of town life. It’s a place to sit down for a cup of coffee or enjoy a few relaxing minutes in the sunshine. In the piazza, you’ll find a 14th century clock tower and centuries-old monuments, along with the requisite shops, post office, and pharmacy of any small town. With few exceptions, most buildings are from 300 to 600 years old. Follow one of the tiny lanes that lead from the piazza and you’ll spot some lovely old mansions. Around the town, much of the original walls remain, along with two of the city gates. With so little evidence of modern times, a visitor will truly feel that Trequanda is of another time. (Perhaps that is why it is so difficult to find!)

A few highlights of this hill town tour include a 13th century church and a municipal palace. The 13th-century Church of Saint Peter and Andrew features a classic checkerboard design on its façade, and frescoes by Italian artists decorate its interior. The Municipal Palace of Trequanda was first built as a residential palace, and it features intricate architectural details. Its interiors include numerous works of art, including lovely frescoes.

Between May and October, visitors can also enjoy a nature train on Sundays. The train passes through several scenic locations in the Siena area, including Trequanda, providing travelers with the opportunity to explore the region’s great natural beauty.

If you truly like to explore sights that are off the beaten track, Trequanda offers the ideal hill town experience.

Whatever villages you choose to explore, you will best experience the charms of a Tuscan hill town in the late afternoon, when you can participate in la passeggiata, the daily stroll of villagers arm in arm through the streets. This communal village custom offers a bit of Tuscan fellowship to visitors the world over.

To learn more about touring Tuscan hill towns, please contact us for more information.

Stuart