Palazzo delle Papesse

The Palazzo delle Papesse stands on Via di Città — the main street connecting Siena's Piazza del Campo to the Piazza del Duomo — a few metres above the descent toward the Campo's curve. The building's Renaissance ashlar facade, its three storeys of molded windows and its distinctive Piccolomini arms above the entrance, is one of the most distinguished on a street of distinguished buildings; it is, consistently, the one that most tourists photograph without knowing what it is.

The name requires explanation. 'Papesse' — 'female popes' or 'papal women' — is the nickname given to the palazzo because it was built for and occupied by the female relatives of two Piccolomini popes. Pius II (Enea Silvio Piccolomini, 1405–1464) was the great humanist pope of the 15th century: a poet, a diplomat, a geographer, and the pope who commissioned the Piccolomini Library in the Siena Cathedral, whose walls are frescoed with scenes from his life by Pinturicchio. His family, one of the most powerful in Siena, also commissioned this palazzo — built by Bernardo Rossellino, the Florentine architect who was Pius II's primary building executor and who also designed the planned Renaissance city of Pienza, 55 kilometres south. Pius III (Francesco Todeschini Piccolomini, 1439–1503) was his nephew, elected pope in 1503 and dead after 26 days in office — a reign so brief that almost no historical record connects to it, but whose Piccolomini family continued to occupy the Via di Città palace.

The palazzo was used from 1998 to 2011 as the Centro d'Arte Contemporanea CCC Siena — a contemporary art centre that used the Renaissance rooms and the courtyard for modern and contemporary exhibitions. Since the CCC's closure, the building has returned to more intimate cultural use. The GYG experience (t1320397, 5.0★, 2 reviews, from $28.50) accesses two elements that are not available on ordinary walk-in visits: the internal loggia courtyard and the panoramic rooftop terrace.

The courtyard wine tasting takes place in the Renaissance loggia — the colonnaded ground-floor gallery that faces inward to the palazzo's private garden and creates the characteristic light-and-shadow architecture of the Italian palazzo courtyard tradition. Tuscan wines are served here; the exact selection varies by session. The setting combines the quality of Sienese 15th-century stonework with a working wine experience in a space that the street facade gives no indication of existing behind it — a classic interior-concealing Sienese palace reveal.

The panoramic terrace, accessible as part of the same experience, offers views that are difficult to replicate elsewhere in Siena at this height and this proximity to the Campo. The Torre del Mangia — the 14th-century civic tower, 102 metres, the second-tallest medieval tower in Italy — is directly visible. The Duomo's striped marble facade and the Gothic campanie close the view to the north. The Tuscan countryside — the Crete Senesi's clay badlands to the southeast, the Chianti hills to the north, the ridge of Monteriggioni to the northwest — fills the far distances on clear days.

The 18+ requirement (explicitly stated in the GYG listing, which also notes it is not suitable for pregnant visitors) reflects the wine-tasting format and the intimate, adult-oriented atmosphere of the experience. This is not a family monument visit but a small-group cultural wine experience in an extraordinary space. The non-refundable booking policy should be noted before committing — as GYG describes it, the product is non-refundable regardless of weather or other circumstances.

Siena's UNESCO World Heritage historic centre (inscribed 1995) is the wider context for the palazzo visit. The city is one of the best-preserved medieval Italian cities — the Campo (the world's finest piazza, arguably), the Duomo, the network of medieval contrade (neighbourhood associations, each with their own church and museum), and the street pattern that 20th-century development barely touched are all within walking distance. The Palazzo delle Papesse visit is most naturally combined with a full Siena day: the Campo in the morning, the Duomo and Piccolomini Library mid-morning, Via di Città and the palazzo wine experience in the late afternoon.