Italian Festivals Palio di Siena The Palio di Siena is a horse race that is held twice each year, on 2 July and 16 August, in Siena, Italy. Ten horses and riders, bareback and dressed in the appropriate colors, represent ten of the seventeen contrade or city wards.A pageant, the Corteo Storico, precedes the race, which attracts visitors and spectators from around the world.The first Palio took place in 1633.The race itself, in which the jockeys ride bareback, circles the Piazza del Campo, on whi