Reasons Why You Should Visit Pienza, Italy

Like any self-respecting Tuscan town, Pienza is home to a host of elegant churches. The town’s cathedral, Cattedrale dell’Assunta di Pienza, boasts a gleaming limestone facade, high, painted naves and Gothic windows that were already becoming retro by the time it was completed in 1462. Also worth the short walk out of town is the Romanesque chapel Pieve di Corsignano. This 12th-century church is where local hero Pope Pius II was baptised.

Pienza was originally a small Sienese village called Corsignano, but when a pope is born in your town, it gets a rename and a fitting makeover. Enea Silvio Bartolomeo Piccolomini went on to become Pope Pius II, but he didn’t forget his hometown, completely rebuilding it so it became a refuge from Rome fit for His Holiness. Piazza Pio II, the town square, is flanked by the cathedral and the Palazzo Piccolomini, which was the pope’s principal residence and boasts a stunning Renaissance garden. Other historical buildings of note are the town hall, Palazzo Comunale, and Palazzo Vescovile, a Renaissance palace complex built by Cardinal Rodrigo Borgia of the infamous Borgia family.

Every Valentine’s Day, Pienza sees the arrival of local tourists who come to stroll the four cobbled streets with quirky romantic names. The four tiny alleys that link the town’s main artery, Corso Rossellino, to Via del Casello are called Via dell’Amore (Love Way), Via del Bacio (Kiss Way), Via del Buia (the Dark Alley) and Via della Fortuna (Lucky Alley). Cute.

Enjoy the best cocktails in town at Idyllium Bar on Via Gozzante, where you can grab a table on the terrace for a breathtaking view of the surrounding hills. Their signature menu includes the Risky Sour, Sex on the Hills and Tusca Libre – fun local plays on international favourites. But if a wine or spritz is more your thing, do as the purists do and hit up Bar II Casello at sunset for more stunning views of the valley tumbling below, plus a great tapas menu.

One of Pienza’s finest dining options is La Terrazza del Chiostro, a high-end delight set in the cloisters and gardens of a 15th-century monastery. Unsurprisingly, pecorino cheese is a key ingredient in a number of offerings – but save room for the cheesecake, presented with fresh peach foam, apricot soup and red wine sauce. For more traditional Italian fare, there’s always the cosy Osteria Baccus on Corso Rossellino, where platters come piled high with local pecorino toscano, truffles, bread and cured meats.

Drive an hour south from Pienza and you’ll arrive at Italy’s largest dormant volcano, Monte Amiata. Hikers, cyclists and horse riders alike can take advantage of the nice range of trails in the region around the south Tuscan mountain. The shortest, from Selva to Selvena, comes in at just 1km (0.6mi), while the longest – the Mountain Ring – is a meatier 24km (15mi). Take your pick.

Pienza is a great base for exploring the neighbouring hillside towns of Val d’Orcia, this central Tuscan region of rolling, lush hillsides, vineyards, cypress trees and the occasional hilltop settlement. Medieval Montepulciano is just a 20-minute drive east of town, and scenic Montalcino can be reached in 30 minutes heading west. Both Montepulciano and Montalcino are wine-lover’s meccas, worth visiting for the vineyard tours, wine bars and incredible hillside views.