Traveling the Via Chiantigiana is like stepping back in time. Here everything has been immortalized, frozen like in a painting by a Romantic artist, but this is an ever-changing land that never stays the same, month after month, season after season, creating a truly extraordinary place.

 

Here the cohesion of the land with the loving labour of farmers reaches the apex of its expression, an unbreakable bond that led to the breathtaking natural landscape and world-famous food and wine. We’re talking about one of the most beloved destinations anywhere on earth, which everybody dreams of seeing at least once in their lifetime. The good news is that you can visit it right now with our imaginary tour through the rolling hills and verdant vineyards.

Via Chiantigiana, the Chianti road, starts south of Florence, near Badia di Ripoli. A short distance from the Renaissance city, this marks the beginning of our southerly tour, into the heart of the Florentine Chianti. 

After only a few kilometres you come across Ponte a Ema, home to the Gino Bartali Cycling Museum, a pillar of local modern history and heroism, a tribute to an extraordinary 20th-century man who became the stuff of legends. 

Continue to the little town of Grassina and keep driving through the Ugolino area: on the left you see the renowned Golf Club: 50 hectares of grassy greens comprise an 18-hole course, a paradise for golfers. 

You’re at the gateway to Chianti and once you reach Strada in Chianti the tour carries on to Greve in Chianti. This stretch of road is perfect for villa and castle spotting, priceless real estate and pieces of history that dot the hills carpeted with vineyards.

Arriving in the Val di Greve, you know you’ve reached Chianti. The scenery starts to hum with the shades and shapes captured in glossy magazines and social media channels. Vineyards and castles dominate the landscape. To see the vineyards all you need to do is look along the road, wind down your windows and gaze as far as the eye can see. To see the castles, you’ll inevitably need to take a detour.

Vicchiomaggio is the first castle along the route, perched on a hill off to the right, near Le Bolle. Converted into a villa in the 16th century, the castle maintains its original 13th-century tower and is surrounded by enticing Italian-style gardens.

Back on the Via Chiantigiana road, the next hamlet is Greti. Immediately after crossing the river Greve, you’ll find the road that leads to Verrazzano castle on your right, birthplace of the great explorer Giovanni da Verrazzano, discoverer of New York Bay, whose family originally owned this place. Here too only the 13th-century tower remains intact, while the remainder was turned into a villa.

Back on our original route, take one last detour just before reaching Greve, a road on your right, which will take you to Villa Calcinaia, ancient in origin, owned by the Capponi counts. This villa also boasts a beautiful Italian garden.

That was the last detour before arriving in the pretty town of Greve in Chianti and its famous Piazza Matteotti. 

Your Chianti tour doesn’t end here of course; there’s one last thing you need to know. The castles and villas scattered throughout the countryside are now well-known wineries vaunting centuries of history. Their walls contain the true treasure of this land, something that makes Chianti world famous. Guess what?