There are two central train stations in Chianti: one in Poggibonsi and the other in Castellina that connect Florence and Siena. You need to change trains at the Empoli train station if you're coming or going to Florence.

The Chianti wine region does not have a single central station that serves the entire area, primarily because the rugged, vineyard-covered hills are not easily traversed by rail. However, travelers can access the region via two main "gateway" stations: Poggibonsi-San Gimignano and Castellina in Chianti-Monteriggioni. Both are located on the railway line connecting Siena and Empoli (where you can transfer for Florence). Once you arrive at these stations, you must typically take a local bus or rent a car to reach the famous villages like Greve, Radda, or Gaiole in Chianti. For many, this lack of direct rail access is part of the region's charm, as it has preserved the landscape from industrialization. If you are staying in the heart of the countryside, a car is highly recommended, as bus schedules in the hills can be infrequent and difficult to navigate on weekends.