Dievole's blog

Tuscany off the beaten path: 3 towns other people have missed

The traveler sees what he sees. The tourist sees what he has come to see.”

― G.K.Chesterton

Tuscany has long been a destination for those looking to escape daily life and throw themselves into Italian culture, renting a beautiful Tuscan villa, enjoying great food and fabulous Italian wines. Florence, Siena, Pisa and San Gimignano being the most famous in this large region full of hidden corners and secret hamlets. While we won’t get into depth on the bigger, more famous cities in Tuscany, we do plan on touching on a more ‘off the beaten’ look at one of the most recognizably famous travel destinations in the world. You can come to this region a 100 times but it still might not be enough, we suggest savoring each place individually and thoroughly, exploring an unknown street, spending a few hours in a local trattoria – talking to a friendly shop owner, even getting lost. While planning your next trip to Italy, we suggest browsing these towns along your journey, while less famous, they are no less Tuscany.

Anghiari (Arezzo)

A town many haven’t heard of, but really should – we love Anghiari for its beautiful medieval town center and stunning views of the Tiber valley, located between the arno and tiber rivers. The town is most famous for the Battle of Anghiari, on June 29th 1440 which assured Florentine rule in the region. It is also depicted in a famous painting, hung in the Palazzo Vecchio in Florence, Italy by Leonardo da Vinci. It’s impossible not to find this area charming, artisan shops, small churches line the winding streets – to get there just look for signs for San Sepolcro or Città di Castello from Arezzo.

What not to miss: Palazzo della Battaglia, Ravagni Oil Mill, Museo Statale di Palazzo Taglieschi (to learn about the Battle of Anghiari).

When to go: in July: during the annual Anghiari Festival (classical music, opera and more).

Where to eat: Instead of lunching in Anghiari, head to the historical center in Arezzo to eat at La Lancia d’oro, in Piazza Grande.

Monticchiello bici

Photo by Georgette Jupe

Castelnuovo Berardenga (Siena)

A charming Tuscan town located in the Chianti Classico wine region, located close to the Tuscan city of Siena and once thought to have been home to Etruscan settlements. The name comes from Count Berardo, a descendant of the Count of Siena Guinigi and was once split into two factions when under the rule of the Grand Duchy of Tuscany to be later reunited in the 1770s. A great place to go on a bike tour, visit wineries and be in a generally wonderful peaceful place.

What not to miss: Home to several beautiful villas, the Landscape Museum and Saint Clemente Church (housing ‘Virgin and Child’ painted by Giovanni di Paolo)

When to go: During the grape and wine festival in the summer and really anytime!

Where to eat: Enoteca Bengodi

Val d'Orcia

photo by Georgette Jupe

 Monticchiello (Val d’Orcia)

The Val d’Orcia national park is a UNESCO heritage site and home to many picturesque towns such as Pienza, known for its famous pecorino sheep chees, Bagno Vignoni with famous thermal baths, Montepulciano and Montalcino, both well known for their wine production. Many instead, never stop by or have even heard of the ‘terrace of Tuscany’, the beautiful village of Montecchiello – close to Pienza, a place that has been around since 900’s when Lamberto Aldobrandesco surrendered the castle to the Badia Amiatina. We personally consider it as one of the most picturesque places in the Val d’Orcia region, plus the center of town is very well maintained. People are friendly and helpful and it helps that the food is top notch as well in this area.

What not to miss: A town best left to wanderers, walk along the Porta Sant’Agata (outside gate – you can’t miss it!) for stunning photos, visit the main church, Church of Santi Leonardo and Christoforo and stop by a local shop for hand-sewn fabrics local to the area.

When to visit: the end of July and August, when the entire town participates in the marvelous Teatro Povero di Monticchiello: The poor Theater of Monticchiello in the main square of the village.