A Chianti Road trip will give you the opportunity to enjoy one of Tuscany’s most charming landscapes. And a drive along the Chiantigiana Road (SR222) that winds its way amongst rolling hills and silvery olive groves, is one of the most magnificent of them all.

Along this route, the colours of the countryside are magnificent in every season. In spring poppies and lilies dot the fields. In summer the vineyards are at their peak, and by autumn they start to paint the landscape with every shade of orange and red. You’ll savour all the different shades of green too. The silvery green of the olive trees, the intense and vivid green of the grass and the vines in summer, and the darker shades of the woods.

chianti road trip

Chianti Road Trip itinerary – Greve in Chianti to Panzano. In search of the best meat in Tuscany.

This itinerary starts in Greve in Chianti, the gateway to the Chianti region. It has a delightful main square surrounded by porticos and pottery shops. A stop at the Antica Macelleria Falorni is a must. Even if you don’t buy anything it’s worthwhile poking your head in, for this is the Gucci of butchers.

A short detour will lead to the tiny hamlet of Montefioralle, perched on a hill, 3 km. from Greve. Leave the car in the parking just outside the wall (piazza Santo Stefano) and walk the narrow cobbled streets of this small borgo that started its life as a castle. Get the camera ready for some very picturesque scenes.

Top tips on How to Plan a Road Trip to Tuscany.


After that carry on your Chianti road trip along the SR222 (Chiantigiana Road) to Panzano. This small town is the perfect place to have lunch. Here the renowned Dante-quoting butcher (so called by the New York Times the world’s most famous butcher) Cecchini has a wonderful shop. Above it there’s a Tuscan style fast food place or try his restaurant called ‘Solo Ciccia’. Afterwards you can walk off your lunch on the way to the Church of Santa Maria. Then it’s back to the car for a relaxing drive to Radda in Chianti.

⇒ Discover 10 Charming small towns to visit in Tuscany.

top 10 destinations in tuscany

Radda in Chianti to Brolio Castle – Chianti magic at its best

The SP2 offers a 13 km. drive to Radda in Chianti that has some awe-inspiring views. The winding road passes through lush vineyards and olive groves in preparation for the most attractive of Chianti small towns, Radda. As you approach it, you’ll see the town on your right, peacefully perched on its hill, surrounded by a sea of green. Its position is truly spectacular.

Atmospheric Radda will welcome you with its Medieval walkway and main square, where the Palazzo del Podestà displays its coats of arms and elegant arches. This palace had been the headquarters of the Chianti League, a military-political organisation that controlled this territory under Florence rule, for over four centuries. Opposite there’s the Neo-Romanesque Church of San Niccolò.

⇒ Find out about 20 Experiences in Tuscany that will make your trip truly special!

radda in chianti
Radda in Chianti

As you drive south along the SP2 and SP484 towards Brolio Castle, the landscape changes. You’ll see fewer houses and pass though some thick woods. At the time of our trip, in April, we saw many hoopoes, which are usually a rare sight.

When you spot the Brolio Castle, up on the hill, surrounded by high cypress trees and imposing walls, you can easily imagine another side of Chianti. For centuries it was not the idyllic region dedicated to the good life that we experience today, but a land of war and powerful lords. For a stunning view, visit the castle’s gardens. From up there you dominate the valleys and enjoy the million shades of green that this region has in its colour palette. Then it’s time to leave the castle and carry on along the SP484.

Find out the best places to visit in Chianti, and the Top things to do in this wonderful region.

chianti road trip
Brolio Castle

San Gusmè and dinner in Castellina in Chianti

A stop in the diminutive walled village of San Gusmè is a treat. Almost lost in an ocean of vineyards, this is a place where time truly seems to have stopped. You’ll find a stone square, few inhabitants and plenty of peace and quiet. San Gusmè is located 29 km. north east of Siena.

For a perfect finish to your Chianti Road trip, head back to Radda and take the SR429 to Castellina in Chianti. Here you can have a special dinner or wine tasting under the atmospheric via delle Volte, a Medieval stone walkway. This attractive small town is alive with enoteche and shops. It’s a real food and wine paradise.

TIME: ONE DAY – 90 km.

=> Top 10 Towns to visit in the Chianti region

chianti vineyards

If you like the idea of a driving holiday in Tuscany, you’ll find plenty of scenic routes to choose from. This One Day Itinerary explores the Less Travelled Part of the Chianti.

⇒ For more suggestions for your trip, check out the 10 top destinations in the region.

⇒ Here’s some itineraries you might find interesting, and a 4 day road trip to the Maremma.

chianti road trip