One of my favorite little towns in Tuscany, incredibly charming and quaint, leaves me longing to return even though there are not an abundance of touristy things to do there.

My heart belongs to Pienza, a tiny medieval town with grand ambitions. Without fail, with each visit, I turn into a romantic dreamer. I want nothing more than to live ‘La dolce Vita’ in this enchanted warren of narrow, cobblestone roads, old stone buildings with colorful wooden shutters and window boxes overflowing with pretty flowers.

Pienze is the heart of the Val d’Orcia between the towns of Montepulciano and Montalcino in the province of Siena. In 1996, Unesco declared the town a World Heritage site, and in 2004 the entire valley surrounding the town was included on the list of World Cultural Landscapes. This small village bursts with history and the most amazing views over the Val d’Orcia.

Pienza, formerly known as Corsignano, is the birthplace of Enea Silvio Piccolomini, who, later in life, became Pope Pius II. Showing an adoration for the place of his birth he used the power and wealth of the papacy to turn Pienza into a model Renaissance town. He hired architect Bernardo Rossellino to build a Duomo, Papal Palace and Town Hall. The construction of these buildings was completed in only three years and, while this famous son of Pienza would have liked to have done more, he died before his ambitions were fully realized. Pienza is now left with a magnificent piazza, Piazza Duomo, that is incongrous with the rest of the small town.

Pienza’s other claim to fame is an exceptional sheep’s milk cheese, or more correctly, ewe’s milk cheese, pecorino. In fact, most of the cheese eaten in Tuscany isn’t cow’s milk cheese but pecorino that is farmed locally. Pecorino d'Pienza is one of the most sublime and sought after of Tuscan pecorino's. Interestingly, on the first Sunday in September a ‘cheese rolling’ competition is held in Pienza, known as “Gioco del Cacio al Fuso”. The participants of this popular festival attempt to roll a small wheel of cheese with the winner being the one who managed to have it stop closest to a spindle erected in the middle of a set of circles drawn on the pavement in the Piazza Duomo. This peasant tradition has been a pastime for generations – a game that each family would play in their own yards.

It is this history and traditions make this Tuscan gem so unique. What could be more romantic than strolling on the Via Amore or enjoying a sunset viewed from the ancient town walls high above the Val d’Orcia.

My personal preference and the undeniable beauty of this hill town made it part of our “Bella Toscana Tour” itinerary and maybe you will fall in love with it too.

Piccolo Pienza