The Wine Road in Chianti, the Chiantigiana (or simply SR 222), is the road that connects Florence to Siena: one of the most beautiful driving routes in Italy, passing through acres and acres of vineyards producing the famous Chianti Classico DOCG.

Chianti has been one of Italy’s most important wine regions for over three centuries. It was here that the family of the Grand Duke of Tuscany began cultivating the vine in the XVIII and XIX centuries in the region that would become modern Chianti.

The Chiantigiana winds its way with a series of zigzags offering enchanting views of the Tuscan countryside, charming medieval villages, and of course, delightful wines to taste.

For a truly stimulating tour of the Chiantigiana, take the time to visit at least some of the ancient towns along the route and explore the vineyards. Most wineries are open to the public, but be sure to check carefully before visiting to avoid disappointment.

When is the best time to travel the Chianti wine road?

The best time of year to visit Tuscany is during the September grape harvest or just before seeing the Sangiovese vines bend under the weight of ripening grapes, the variety from which Chianti Classico is produced.

Another good reason to go in September is to participate in one of the local festivals celebrating the harvest, such as Vino al Vino, held the third week of September, in the small town of Panzano, where you can taste numerous local wines by the glass.

What to do along the Chiantigiana

• Visit wineries: The Wine Road is home to numerous wineries, where you can taste local wines and learn about the wine production process. Many wineries also offer guided tours of vineyards and production facilities.
• Taste local food: Chianti Classico DOC Vinsanto, a liqueur aged for up to 5 years in small wooden barrels called “caratelli” and produced from Malvasia bianca and Trebbiano grapes; Chianina meat, handmade pasta, and cured meats, including pork, wild boar, and cinta senese pork.
• Explore villages: Characterized by narrow streets, houses with red tile roofs, and ancient churches.
• Go hiking: The Wine Road is a paradise for hiking enthusiasts. There are trails for all levels of difficulty, crossing vineyards, woods, and meadows.
• Visit castles: Along the Wine Road, you’ll find numerous castles, with a small detour towards Arezzo you can also find the Castello di Gargonza with its typical village.
• Go cycling: The Wine Road is a great destination for cycling enthusiasts. There are cycling routes for all levels of difficulty, offering breathtaking views of the hills and vineyards.
• Relax: An ideal place to relax and enjoy the peace and tranquility of the countryside. There are numerous agritourisms and hotels offering a welcoming atmosphere and impeccable service.

How to plan your trip along the Chiantigiana

Here are some tips for planning your trip on the Wine Road:

• Choose the best time to travel: The wine road is beautiful to visit all year round, but the best times are spring and autumn when the weather is mild and the vineyards are in bloom or fruit.
• Book your accommodation in advance: The Chiantigiana is a popular tourist destination, so it’s important to book your accommodation in advance, especially if you’re traveling during peak season. You can take advantage of a unique stay in a castle.
• Rent a car: The best way to explore the Wine Road is by car, if you arrive by train or plane make sure you have a car available to stop where you want and visit the wineries and villages that interest you the most.
• Wear comfortable shoes: If you plan to hike or walk, wear comfortable shoes and layered clothing.
• Bring a camera: The Wine Road is a truly picturesque place, so don’t forget to bring a camera to capture your memories.