If you're on a wine tour of Italy or just want to explore one of its beautiful rural areas, your travels might lead you to the Chianti region of Tuscany. Wedged between Florence, Arezzo, and Siena, Chianti is a hilly region filled with rolling vineyards that produce the famous namesake wine. Many of the towns in the region offer tasting rooms where you can sample and purchase wine from a number of different area wineries.

Because Chianti is dotted with small towns and its wineries are in the countryside, it makes the most sense to visit the area with a rental car or private transfer, taking in the wineries near Radda, Castelnuovo Berardenga, Greve and other charming towns.

You can visit the Chianti region from Florence en route to Siena with stops at towns and wineries along the way. The 60-mile (97 km) trip can be done in a long day or can be broken up with overnight stops. While it's easy driving in this region, hiring a driver allows you to enjoy wine tastings and winery visits at your leisure and let someone else worry about the driving. 

From Florence

Duration: 2-2.5 hrs to Siena, by car

If you're traveling from Florence, your getaway to Chianti might start in Greve in Chianti, one of the main wine towns in the region and the one closest to Florence. From Florence's city center, the 20-mile (30 km) drive to Greve takes about 50 minutes. Leaving Florence, follow signs for the SS222 in the direction of Siena or Greve-Siena. This road is also signposted SR222/Chiantigiana, and leads directly to Greve in Chianti. 

From Greve in Chianti, a typical wine tour might continue on to Radda in Chianti, an overnight stop on this 6-Day Getaway to Tuscany and Rome. Radda is 11 miles (18 km) from Greve. The winding drive takes about 30 minutes and passes vineyards and farmland along the way. 

From Radda, it's 17 miles (28 km) to Castelnuovo Berardenga, which is a stop on this 7-day bike tour along the famous Eroica Wine Route in Tuscany. From Castelnuovo, you can follow the SP7/SS73 12.5 miles (20 km) to Siena.

If you want to bike the whole distance from Florence to Siena, this 5-day cycling itinerary includes an overnight stay in Radda in Chianti. 

Of course, your driving route can be reversed by beginning in Siena and ending up in Florence. 

From Rome

Duration: 3 hours by car to Radda-in-Chianti, 3.5 hours by train and car

If your trip to Chianti begins in Rome, you can take any one of dozens of daily Trenitalia or Italo trains from either Termini or Tiburtina stations in Rome to Florence's Santa Maria Novella station. From there, connect to a regional train into Figline Valdarno and take a taxi from there.

You can also go by road, a journey of about three hours. While there are bus connections from Florence to some of the towns in Chianti, for ease of travel – and getting to those rural wineries – a rental car or a private driver still make the most sense if you want to go by road.

Learn more about getting from Rome to Radda-in-Chianti