Follow La Strada del Chianti (SR222) and stop along the way to your heart’s desire. Etruscans were first here, then Romans drove their carts on these roads. A land of tremendous beauty and forever radiating serenity, the wine road witnessed the obsessive conflicts between Florence and Siena, undisturbed by battles and the march of time. Around its winding path, the timeless villages, sun-drenched vineyards, and fortified castles of Chianti Classico unfurl. Look for the Black Rooster (Gallo Nero), the historic symbol of this renowned wine, marking the territory.
One way to go is from the formidable, perfectly walled Monteriggioni up through Castellina in Chianti to Panzano, where the legendary butcher Dario Cecchini holds court, and Greve in Chianti. Another one goes from Castellina towards Radda and the unique hamlet of Volpaia, then circles towards Gaiole, passing through San Felice to the gates of Brolio Castle.
In Castellina, walk the Via delle Volte and visit the Rocca Comunale, the ancient town hall. In Tavarnelle you can stop at a local tavern to honor the name – Tavarnelle is derived from the Latin word taberna (tavern). In Greve, take your time for lunch or coffee in the central piazza and do a bit of food shopping — salame di cinghiale (wild boar salami) at the meat-heaven Macelleria Falorni. Then drive uphill to Montefiorale, a secret gem, almost always overlooked while passing through Greve. This tiny fortified village is rated one of the most beautiful in Italy and it is also one of the oldest, still preserving the original walls. If you arrive in September, during harvest season, you will enjoy the discreetly sublime Montefioralle Divino, a wine tasting festival where local producers showcase their Chianti Classico wines (Annata, Riserva, and Gran Selezione).
Then there’s Volpaia – oh, how I adore the not-so-famous Volpaia! This is a truly unique community of organic farming and ancient winemaking, worth losing your head over. Come for a glass, forget time, stay for the night. Osteria Volpaia is culinary marvel – think bread ice cream meets pecorino, caramelized apples, and black pepper – but the thing you cannot leave without is one bottle – or three – of their Coltasala wine. So it goes.
If you really know your Chianti, you must pay your respects to Castello di Brolio. This formidable castle passed to the Ricasoli family in 1141. Their family tree, captured in a 1584 print, is one of Chianti’s earliest visual records. It was Bettino Ricasoli, the “Iron Baron,” a key figure in the Italian Risorgimento and later Prime Minister, who became the true father of Chianti Classico. In 1872, he perfected the wine’s enduring formula of a minimum of 80% Sangiovese grapes. Today, Barone Ricasoli stands as the oldest winery in Italy and the fourth longest-lived company in the world still active at its birthplace.
