Traditional festivals: the Bravio delle Botti, a race which dates back to the 14th century between the eight districts of Montepulciano (Cagnano, Collazzi, Gracciano, Coste, Poggiolo, San Donato, Talosa, and Voltaia) on the last Sunday of August. In the city's main streets spingitori (runners) roll an 80 kg barrel from Colonna del Marzocco to the cathedral forecourt on Piazza Grande.
To think about
The agritourism places are often located on hidden minor roads that are rather poorly sign-posted. Even a GPS sometimes has difficulty finding them. Here are few pieces of advice: (1) stay calm, (2) make sure you have a good, detailed map of the area, and (3) do not hesitate to flag down passersby for directions.