Beautiful Pienza: A Veritable Chianti Highlight

The region might be best known for its wine, and rightly so, but there are many more things to do in Chianti than sample its vintages. From exploring classic Italian culture and architecture to taking in the beautiful scenery, this article introduces the lesser known town of Pienza - a wonderful hilltop town that makes for a lovely day trip while you’re in the area. 

A Unique History 

As with many of the best Italian destinations, Pienza is inextricably linked to the Renaissance. But even with competition like Florence and Venice, Pienza stands out. 

It started life as the small village of Corsignano, but was transformed after native son Enea Silvio Piccolomini became Pope Pius II in 1458. A committed humanist, the new pope set about transforming his birthplace into the ‘ideal town’, rebuilding it according to utopian urban planning. 

Today it’s a UNESCO World Heritage Site, and the interesting range of attractions in the town are testament to its fascinating history . 

Excellent Architecture 

It wouldn’t be an Italian travel destination without beautiful buildings, and Pienza is full of great sites that provide some of the best things to do in Chianti. 

Cattedrale dell’Assunta 

In addition to the unique octagonal bell tower that dominates the town’s skyline, this classical-inspired duomo holds paintings by some of the era’s best artists. 

Piazza Pio II 

The central square is a great place to wander, with the beautiful ‘well of the dogs’ a popular tourist attraction for centuries. While you’re here, though, you should pay attention to the feel of the space – it was designed to instil feelings of dignity and solemnity in all that walk around it. 

Palazzo Piccolomini 

Finally, beside the cathedral sits this elegant, trapeze-shaped palace. Intricate details offer lots of photo opportunities, while the covered-roof loggias are blanketted with hanging gardens that provide stunning panoramic views of the surrounding valley. 

A Fun-Filled Festival 

It’s not available all year round, but if you’re lucky enough to visit in early September, Pienza’s Fiera del Cacio festival is one of the very best things to do in Chianti. Dedicated entirely to local produce and crafts, it’s a great opportunity to pick up some gifts for those at home while also seeing a unique side to the region. 

Don’t Miss: The Palio del Cacio Fuso – a game central to the celebrations, where players from each of the town’s districts roll cheese wheels around a wooden spindle in the central square. It’s quite a spectacle!

Fine Food 

Of course, we couldn’t finish this article without mentioning some of the excellent food to be found in Pienza, and while there’s all the great wine you’d imagine on offer here, Pienza is ultimately known for one thing: its cacio, or cheese. Made from sheep’s milk and aged to perfection, with a range of tastes from mild to strong, the town’s Pecorino is its pride and joy – don’t leave without trying some, and you’ll understand why it’s so famous! 

Top Tip: If you want to taste local produce prepared by people who really know what to do with it, you can’t miss Osteria Baccus. From bruschetta and pici to a hearty fondue, this excellent restaurant is always worth a visit. 

Located between Montalcino and Montepulciano, Pienza is easy to get to, and a visit is one of the best things to do in Chianti. Make sure not to miss out when you make your trip to Tuscany! 

Author Plate

Mauro Bramante is the Director of WalkAbout Florence, an independent business offering unforgettable tours and excursion around Italy including the best things to do in Tuscany. Whether you want to ride a Vintage Vespa, try the famous Chianti wine or get cooking with fresh local ingredients, Mauro's company promises excitement, adventure and above all, fun. If you're keen to experience the magic of Italy with the help of some passionate and knowledgeable tour guides, look no further than WalkAbout Florence for your next getaway.