Tuscan Roadtrip: Pienza and Montalcino in Val d’Orcia

Iconic cypress trees, scenic drives, pecorino cheese, Brunello wines, Pienza and Montalcino in Val d’Orcia is a must!

Using Montepulciano as a base, we took two separate day trips to Pienza and Montalcino. In theory, you can visit both hilltop towns on the same day if you have stamina. But we like slow travel these days especially with a young kid in tow. Besides, driving around the Tuscan wine country is as scenic as it can get. 

Views from Pienza

A short 20 minute drive with classic views of cypress trees from Montepulciano takes you to Pienza. It is perfect as a day trip, along with a leisurely hike or some winetasting. A beautiful Renaissance town in the Val d’Orcia region, Pienza is a UNESCO World Heritage Site redesigned by Pope Pius II. It is famous for the delicious production of the salty, yet nutty sheep milk pecorino cheese.

It was a glorious sunny day. With our tummies grumbling, we ordered sandwiches at the popular La Tana Del Goloso to eat off the “Streets of Love”  (Via del Bacio, Via dell’Amore, Via della Fortuna and Via del Buia). We enjoyed the warmth of the sun and the lovely views of Val d’Orcia and Duomo di Santa Maria Assunta. The pedestrianised streets are delightful as are the notable landmarks including: Palazzo Piccolomini, the Duomo, and the Palazzo Comunale. 

For movie buffs, there is a famous scene in The Gladiator just outside the walls of Pienza where Russell Crowe walks through miles of golden fields. You can relive the cinematic scenes by following the road V. delle Fonti until you reach the 12th century Romanesque church Corsignano. Unfortunately for us, the wheat fields had already been harvested and ploughed through. But we still enjoyed the walk if only to burn off the calories from the porchetta sandwiches! A lovely afternoon in beautiful Pienza. 

Views from Montalcino 

Another 20 minutes from Pienza along the same road  is the magical hilltop town of Montalcino. If you are a wine enthusiast and nature-lover, you cannot go wrong using Montalcino as a base. Compact in size and picturesque, the entire village is charming with numerous wine shops  and cozy bars.

Nearby are plenty of wineries but due to the winter season, we did our tastings in Montalcino. Fortezza di Montalcino is a great wine bar/shop especially with kids in tow. Firstly, you can walk the circumference of the fortress as a family, enjoying the amazing views of the village and countryside. Secondly, the plaza is completely car-free so you can enjoy a glass of wine whilst the little ones run around. Brunello di Montalcino wines are made exclusively from 100% Sangiovese “Brunello” grapes with a minimum aging process of at least five years, of which two years should be in oak barrels and no less than four months in the bottle. The knowledgeable staff was very friendly, helping me pick out six wines to take back to London. 

In the heart of Val d’Orica, the hilltop towns of Pienza and Montalcino is a must on your Tuscan itinerary. 

Next up: Firenze or Florence!