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If you come by car, you're better off leaving it in one of the parking lots around the perimeter of town, as driving is nearly impractical in most parts of the city center. Practically unchanged since medieval times, Siena is laid out in a "Y" over the slopes of three hills, dividing the city into terzi (thirds). Although the most interesting sites are in a fairly compact area around the Campo at the center of town, be sure to leave some time to wander into the narrow streets that rise and fall steeply from the main thoroughfares, giving yourself at least two days to explore. At the top on the list of things to see is the Piazza del Campo, considered by many to be the finest public square in Italy. The Palazzo Pubblico at the lower end of the square is worth a visit. The Duomo is a must-see, as is the Cripta.
It's a joy to walk in Siena—hills notwithstanding—as it's a rare opportunity to stroll through a medieval city rather than just a town. (There is quite a lot to explore, in contrast to tiny hill towns that can be crossed in minutes.) The walk can be done in as little as a day, with minimal stops at the sights. But stay longer and take time to tour the church building and museums, and to enjoy the streetscapes themselves. Several attractions have reduced hours Sunday afternoon and Monday.
At the top of the Campo is a copy of the early 15th-century Fonte Gaia by Siena's greatest sculptor, Jacopo della Quercia. The 13 sculpted reliefs of biblical events and virtues that line the fountain are 19th-century copies; the originals are in the museum complex of Santa Maria della Scala. On Palio horse-race days (July 2 and August 16), the Campo and all its surrounding buildings are packed with cheering, frenzied locals and tourists craning their necks to take it all in.
Caterina Benincasa, born here in 1347, had divine visions and received the stigmata, but she is most famous for her words and her argumentative skills. Her letters—many of which are preserved in the Biblioteca Comunale—were dictated because she did not know how to write. She is credited with convincing Pope Gregory XI (1329–78) to return the papacy to Rome after 70 years in Avignon and French domination, ending the Western Schism. Caterina died in Rome in 1380 and was canonized in 1461.
In subsequent centuries, the rooms of the house, including her cell and the kitchen, were converted into a series of chapels and oratories and decorated by noteworthy artists with scenes from Caterina's life. In 1939, she was made a patron saint of Italy, along with St. Francis of Assisi. In 1970, she was elevated to Doctor of the Church, the highest possible honor in Christendom. She has been named a patron saint of Europe but, strangely enough, never of her hometown.
Although the Duomo is celebrated as a triumph of 13th-century Gothic architecture, this church, built at about the same time, turned out to be an oversize, hulking brick box that never merited a finishing coat in marble, let alone a graceful facade. Named for the founder of the Dominican order, the church is now more closely associated with St. Catherine of Siena. Just to the right of the entrance is the chapel in which she received the stigmata. On the wall is the only known contemporary portrait of the saint, made in the late 14th century by Andrea Vanni (circa 1332–1414). Farther down is the famous Cappella delle Santa Testa, the church's official shrine.
On either side of the chapel are well-known frescoes by Sodoma (aka Giovanni Antonio Bazzi, 1477–1549) of St. Catherine in Ecstasy. Don't miss the view of the Duomo and town center from the apse-side terrace.
