One of Tuscany's most anticipated summer events is the Palio di Siena. The most famous horse race in Italy is held twice a year in Piazza del Campo, Siena's main medieval, shell-shaped square. For centuries, the Palio has served as a competition between the city's districts, known as contrade. This historic tradition dates back to 1633, but Siena celebrates it with the zeal of its past every year.

Palio di Siena | When does the Palio take place | Tuscany

The Palio della Madonna di Provenzano takes place on July 2nd, while the Palio della Assunta takes place on August 16th. The first day is dedicated to the tratta, which is the drawing of lots and the assignment of horses to each contrada.

Before the official race, the city hosts six trial runs, one in the morning and one in the afternoon, but jockeys try to avoid overworking their horses. Both races begin with a historic procession and end with open-air dinners in each contrada.

But that's not all: the city holds a Messa del Fantino (Mass for the Jockeys) on the day of the Palio in the chapel next to the Palazzo Comunale.

In the morning there is the “segnatura dei fantini”, or announcement of the jockeys' names, takes place in the Palazzo Comunale and early in the afternoon horses are blessed, followed by the historic parade in Piazza del Campo.

Palio di Siena | The Prize

The Palio prize is the Drappellone, or large drape, or Cencio, a large painted silk canvas designed and created by a different artist each year. During district celebrations, the winning contrada displays the canvas in its museum. The Aquila contrada has the oldest existing Palio, which dates from 1719.