3 Tuscan Hill Towns to Add to Your Bucket List.

We’ve been extremely fortunate to travel all through Italy. Beth and I love the country. We get it. We get the people. We get the food. And most of all we get the passion. Beth still has family there, most of whom still live in Lacedonia—a small hill town in Southern Italy where her grandparents lived before coming to the United States.

During our first trip to Italy in 2010, we spent a weekend in Lacedonia, connecting with family members who had been lost for nearly two decades. Those 72 hours still stand out as some of the most memorable moments from our travels. For some reason, though, it took me several years and a few more trips back to Italy to realize the draw of the country’s hill towns.

My epiphany came as I was sitting on the back patio of Agriturismo La Pietriccia in Tuscany on the first day our Local Living Italy Tour with GAdventures. We were enjoying house wine and cheeses and cured meats as the sun set over Chianciano Vecchia  (the old town of present day Chianciano Terme) on the crest above. Our host, Stefano, was in the kitchen preparing dinner. This is his family’s land, and it has been for a very longtime. The olive oil and house wine were also his as well as some of the cured meats. In big cities, like Rome and Milan, people like Stefano are a rarity. But in Italy’s hill towns, he and others like him are the backbone that meld the country’s past with its future.

Siena and San Gimignano are the most well known hill towns in Tuscany, but they certainly are not the only ones. In fact, central Italy is famous for its hill towns. Their crumbling stone walls seem to cling to every rocky peak, watching over the manicured valleys and vineyards as the rush of the 21st century passes by below. During our stay with Stefano, we visited three hill towns, including Chianciano Terme, in the Siena Province. Each offered a taste of what eludes so many visitors to Italy: tranquility and tradition.

Chianciano Vecchia

Wine tasting in the cellar of Agricola Fontanelle.

Separated by a valley, Chianciano Vecchia is only a 10 minute walk following Via Madonna della Rossa from Agriturismo La Pietriccia. We spent most of our time in Chianciano Vecchia exploring the wines of Agricola Fontanelle. In the cave-like cellars of the small batch winery, we met with winemaker Riccardo Rosati who, along with his two brothers, produces world-class wines from experience they’ve inherited from generations of family winemaking. We spent a few hours with Riccardo and his family, sampling their wines and incredible selection of cured meats and olive oil. The family’s warmth made us feel like locals, just visiting with some friends on a weekday night.

Montalcino

If Virginia is for lovers then Montalcino is for wine lovers. This medieval hill town is famous for its Brunello di Montalcino red wines, featuring an array of enoteche (wine bars). Heck, even the 14th century fortezza contains one. Just outside of Montalcino sits the Abbey of Sant’Antimo. Located in a valley of olive trees, the abbey is considered to be one of the top architectural remains of the Romanesque Period. Several times a day the church’s community of monks fill the 12th century stone hall with the harmonious sounds of traditional Gregorian chants. We got to hear the chants in person and it was mesmerizing. The performances are free and open to the public.

Pienza

A beautiful, typical scene in this perfect Italian town.

Named after pope Pius II, Pienza is full of renaissance architecture, moving with the feel of a modern day medieval village. As I looked out over the gentle, carefully cultivated hills of Val d’Orcia, a UNESCO World Heritage Site, it was easy to see the inspiration behind pope Pius II decision to remodel his hometown in the style of his day: Renaissance. Besides the hill towns’ grand views and classic architecture, Pienza is also known for its sheep’s milk cheese, pecorino. Plus, with streets names like Via Dell’Amore (Love), Via Del Bacio (Kiss) and Via Della Fortuna (Fortune), it is difficult not to fall head over heels for this charming hilltop town.

Do you have a favorite Italian hill town? If so, we’d love to hear about it!

Want more Tuscany? Here’s a few other stories from our Local Living Tour:

Notes From A Small Tuscan Wine Cellar

Biking Through Tuscany: A Photo Journey

Living Like a Local in Tuscany with G Adventures

*Disclosure: While we were hosted by GAdventures, our thoughts and opinions are entirely our own.