The Chianti Classico territory extends itself from Florence to Siena, the two towns that contested it for many centuries. The area entirely englobes the communes of Greve, Radda, Castellina and Gaiole in Chianti as well as a part of Castelnuovo Berardenga, Barberino Val d’Elsa, San Casciano Val di Pesa, Poggibonsi and Tavarnelle. It is a land of hills, covered in forests and dotted with tiny hamlets, castles, ancient churches and farmhouses. Its vineyards, olive groves and dirt roads convey the rural characteristics of the territory.
The Chianti Classico Wine and Olive Oil Trail crosses the whole territory, starting from Greve in Chianti and its triangular main piazza, fronted by numerous medieval buildings and where a market has been running more or less continuously for centuries. It runs straight down towards Siena through Panzano with its 6th century Pieve di San Leolino and then Castellina.
Much of the wine and olive oil trail is, however, made up by the network of roads that connects the bigger towns to the hamlets and castles, like the one going towards Radda in Chianti, already the capital of the so-called Lega del Chianti, unto the Castel of Brolio where in 1874 Baron Bettino Ricasoli created the definite Chianti recipe (70% Sangiovese, 15% Canaiolo and 15% Malvasia Bianca).
Along the wine and olive oil trail there are many guided tours of the wineries as well as places where one can taste wine and olive oil. The principle product obviously is the Chianti Classico DOCG wine which boasts the black rooster seal, Gallo Nero. Another grape product is the Chianti Classico DOC Vinsanto made from the dried white grapes of Malvasia and Trebbiano. The Chianti Classico DOP extra virgin olive oil is made by cold extraction from the Frantoio, Moraiolo, Correggiolo and Leccino varieties. The Chianti Classico area also possesses solid gastronomic traditions with its roots tightly clinging to peasant cooking. Local restaurants have a wide selection of dishes with cheese, cold meat, chianina beef, the cinta senese pork and wild boar. Recently the cultivation of saffron has been resumed.