Pienza is known as the small jewel of the Renaissance in southern Tuscany and has obtained recognition as a UNESCO World Heritage site. It is located southwest of Lucignano near Siena and Montepulciano (~30 min drive from the B&B). The drive there will take you through the rolling hills of the Val d'Orcia and due to the town's position at the top of a hill, the views from Pienza are also breathtaking.
The town, while small, is full of artisan shops, restaurants and history. The city is known as the Utopian City or the "Ideal City of the Renaissance" due to how the founder Enea Silvio Piccolomini (who later became Pope Pius II) embodied the Italian Renaissance spirit. His Italian Renaissance spirit is often described as remembering the past but searching for modern utopian projects, rejecting pessimism, and demonstrating courage while using experience to overcome evil. There is must history to be learned from how the town of Pienza was built including how the buildings are positioned and why, the first European roof garden, Pienza's Duomo and its famous piazza.
Because Pienza is so small, you can easily see both Pienza and Montepulciano in the same day. Montepulciano is only about 20 minutes from Pienza. Tour Pienza and have lunch and then head to Montepulciano for wine tastings, shopping and more sight-seeing. Two great choices for food in Pienza include Al Fierale and Latte di Luna. Latte di Luna has a great patio for outside dining, weather permitting. Pienza is known for its pecorino so a meat and cheese plate starter is a must in this area.
On your way to Pienza (or from Pienza to Montepulciano), stop in Biagiotti, a very well known (for the area) ironworks shop. Even if you are not planning on buying anything, its a great store to browse. The store is known for making things from hand with iron, particularly lighting. It is located right off the main road before you hit the town of Pienza.
Wrap up your day in Montepulciano and taste from Nobile and Rosso di Montepulciano. There are vineyards all around the town which is also perched on top of a hill. You can also find plenty wine bars and tasting rooms inside the medieval walls of the city.
If you are interested in a tour guide for any of these cities and interested in learning a bit more than what a self-guided book might offer, let us know in advance and we can arrange that service for you and your group.