The winner is awarded a banner of painted silk, or palio, which is hand-painted by a different artist for each race. The enthusiasm after the victory, however, is so extreme that the ceremony of attribution of the palio is quite instantaneous, being the first moment of a months-long celebration for the winning ward. There are occasional outbreaks of violence between partisans of rival contrade.

There may be some danger to spectators from the sheer number of people in attendance. There have also been complaints about mistreatment of horses, injuries and even deaths, especially from animal-rights associations and even from some veterinarians. In the Palio held on 16 August 2004, the horse for the contrada of Bruco (the Caterpillar) fell and was badly trampled, as the race was not stopped despite possible additional safety risks for other horses. The horse died of its injuries, raising further complaints from animal-rights organizations.

The Palio differs from "normal" horse races in that part of the game is for the wards to prevent rival contrade from winning. When a contrada fails to win, its historical enemy will celebrate that fact nearly as merrily as a victory of its own, regardless of whether adversarial interference was a deciding factor. Few things are forbidden to the jockeys during the race; for instance, they can pull or shove their fellows, hit the horses and each other, or try to hamper other horses at the start.

The most successful ward is Oca, the Goose, which has won 63 races (at least according to their records, which start from 1644), followed by Chiocciola, the Snail, with 51, and Tartuca, the Tortoise, with 46. Oca is also the contrada with the most wins in recent history (from 1900 to 2010) with 21 victories, followed by Selva, the Forest, with 18, and Drago, the Dragon, with 17.

Among jockeys, the most victorious of all time is Andrea Degortes（英语：Andrea Degortes）, nicknamed Aceto ('Vinegar'), with 14 wins (from 1964 to 1996). Angelo Meloni, nicknamed Picino (active from 1897 to 1933) has the second in the number of wins with 13 successes, and Luigi Bruschelli, nicknamed Trecciolino（英语：Luigi Bruschelli） (still active), has the third most of 12 wins (although he claims 13 victories, his horse won without him one year).

The most successful horses were Folco and Panezio with eight wins each, followed by Topolone with seven.

In recent history (from 1900 to the present), only three wards have ever succeeded in winning both the July and the August races in a single year (the term in Italian is fare cappotto). Tartuca (the Tortoise) accomplished the feat in 1933, while Giraffa (the Giraffe) won both races in 1997, with jockey Giuseppe Pes, nicknamed Il Pesse. In 2016, jockey Jonatan Bartoletti, on the mount "Preziosa Penelope", won both the July and August races for Lupa (the She-wolf).[5]

Ritual and rivalry

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The Palio di Siena is more than a simple horse race. It is the culmination of ongoing rivalry and competition between the contrade. The lead-up and the day of the race are invested with passion and pride. Formal and informal rituals take place as the day proceeds, with each contrada navigating a strategy of horsemanship, alliances and animosities. There are the final clandestine meetings among the heads of the contrade and then between them and the jockeys.[6] There is the two-hour pageant of the Corteo Storico, and then all this is crowned by the race, which takes only about 75 seconds to complete. Although there is great public spectacle, the passions displayed are still very real.

The contrada that has been the longest without a victory is nicknamed nonna ('grandmother'). Civetta (the Owlet) had the title from 1979 until 2009, when it won 16 August race. Torre (the Tower) had this title for being without victory for 44 years (from 1961 to 2005), and Bruco (the Caterpillar) held the title for not winning over 41 years (from 1955 to 1996). Last nonna was Lupa (the She-Wolf), which has not had a victory since 2 July 1989, a period of 35—36 years, until July 2016, when it finally won, leaving now the nonna title to Aquila (the Eagle).

Palio (Drappellone)

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The drappellone banner of the Palio of 16 August 2009, painted by Giuliano Ghelli

The drappellone ("banner"), or palio, known affectionately as "the rag" in Siena, is the trophy that is to be delivered to the contrada that wins the Palio.

The palio is an elongated rectangular piece of silk, hand-painted by an artist for the occasion. It is held vertically on a black-and-white shaft halberd and topped by a silver plate, with two white and black plumes draped down the sides.

The palio, along with the plumes, remains the property of the contrada. The plate is returned to the city of Siena before the two Palii of the following year, after the date and the name of the victorious contrada are inscribed on its back. There is one silver platter for the Palio in July and another for the August Palio. The plates are replaced approximately every ten years.

The value of the banner is unique, because it represents a particular historical period of the city of Siena. The palii often reflect the symbols of the various governments that have presided at various times, including the crest of the grand duchy of Lorraine, the crest of the Grand Dukes of Tuscany, the crest of the Kingdom of Savoy of Italy, symbols from Fascist Italy, and most recently, imagery of the Republic.

The process that an artist should follow in designing the palio is rigid: it must follow a precise iconography that includes some sacred symbols, as the July Palio is dedicated to the Madonna of Provenzano, and that of August to the Madonna of the Assumption. It must present the insignia of the city, those of the third part of the city,[7] and the symbols or colors of the ten contrade participating in the race. There are, however, no limits regarding the style of the art. The palio is first presented at a press conference in the courtyard of the Podestà of the City Hall about a week before the race.

The Palio runs throughout the year

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A typical image of the four-day party: groups of Contrada della Torre (Tower) on stage singing

Although many activities take place within each contrada, the organization of the Palio is still the largest, since it is not just in two races each year. Each time, the festival itself runs for four days of events, the preparation for which lasts all year.

Beginning in early winter, the contrada leaders talk and develop strategies, making contacts with the jockeys and horse owners. These leaders prepare those who will race in the Piazza del Campo or take part in minor Palios elsewhere in nearby towns (la cosiddetta provincia) and bring them to training courses organized by the city in the spring.

The full activities of the Palio start to grow in momentum towards the end of May, with the drawing of lots of the three remaining contrade that will join the seven that have won the right to race. With districts and teams outlined, contrade begin to talk about "deals" (engagement of jockeys) and "parties" (secret pacts for the win), despite not knowing which horse they will draw in the lot.

About a week before the race, the palio (drappellone) itself is presented to the city, which has commissioned a local artist (in the case of the Palio of July) or internationally recognized artist (in the case of the Palio of August or a special Palio) to create the prize. Also at this time, visits occur to the horses which will be presented for the lottery.

In the first of the four days of the festival, the lottery is held to select which barbero (the term for "racehorse" in the city of Siena and Tuscany) will go to which contrada. The stone race track around the square is covered with a layer of dirt composed of a mixture of tuff, clay and sand. Six trials are run, during which the riders have the opportunity to familiarize themselves with their horse and with the track itself, its sounds and rhythms of the race. Although the trials are attended by many tourists and contrada members in square, barriers are mounted on the outside of the track.

Among the events that mark the approach of the Palio are the rehearsal dinner, the "mass" of the jockeys and the blessing of the horse and jockey.

Extraordinary Palios

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An extraordinary Palio is a third Palio which may take place during the period between May and September and is associated with events or anniversaries of major importance for the community of Siena. The last extraordinary Palio coincided with the advent of the new millennium. It was actually held on 9 September 2000 and was won by Selva (Forest), by jockey Giuseppe Pes riding on the horse Urban II. Prior to this, the last extraordinary Palio was held on 13 September 1986 to celebrate the centenary of the abolition of the Balia and Biccherna governments.

In earlier times, the third Palio was a way to honor distinguished guests passing through or visiting Siena. Examples are the extraordinary Palio of 7 June 1676, during the visit to Siena of the wife of Prince Don Agostino Chigi, and that of 15 June 1673 (not considered official), honouring the visit to Siena of Cardinal Flavio Chigi（英语：Flavio Chigi (1631-1693)）. Even the Grand Duke of Tuscany requested another round of Palio, perhaps closer to the ordinary.

From the second half of the 19th century, extraordinary Palios began to be organized for celebration of special events, rather than illustrious visits. This was the case of a meeting of the Society of Sciences or the inauguration of important monuments (such as the inauguration of the monument to the fallen in the Battle of Curtatone and Montanara, on 29 May 1893). In 1896, they even ran four Palios, both ordinary and two extraordinary. The first extraordinary race was on 16 August, which is considered extraordinary because it was requested by the citizens as the original race was moved to 25 August due to transfer from Siena's VIII Corps, and the second was on 23 September for the inauguration of the monument to Giuseppe Garibaldi.

A third Palio, the "Palio of Peace", was held in 1945 by popular acclaim to celebrate the end of World War II and was won by Gioacchino Calabro riding Rubacuori su Folco, for the contrada of Drago (Dragon). An extraordinary Palio was held in 1969 to commemorate the conquest of the moon by the Apollo 11 mission.

The following years created the habit of running on the occasion of a centenary of particular importance. This is the case for 28 May 1950, the fifth centenary of the canonization of St. Bernardine of Siena, and 5 June 1961, the centenary of the Unification of Italy.