The Wine Roads of Chianti Classico: A Day Beyond Florence

The vineyards of Chianti Classico begin where the suburbs of Florence end — and the transition is abrupt. One moment you are in a city of stone and traffic; thirty minutes later, you are standing on a hilltop among rows of Sangiovese vines that stretch to the horizon, with the towers of San Gimignano visible on a clear day.

Chianti Classico — the historic heart of the Chianti wine region, distinguished by the Gallo Nero black rooster on every bottle — produces some of Italy's most serious and age-worthy wines. The Sangiovese grape, in the hands of the region's best producers, achieves a balance of power, elegance, and terroir expression that rivals the great appellations of Burgundy.

Our concierge arranges private vineyard visits to estates that do not normally accept walk-in visitors. A morning at a family-run cantina in Greve in Chianti, where three generations have tended the same vines. An afternoon tasting at a historic estate near Radda, where the cellar is carved into the hillside and the Riserva ages in Slavonian oak barrels for thirty-six months.

The experience extends beyond wine. Many estates offer seasonal lunches prepared with ingredients from their own farms — cold-pressed olive oil, aged Pecorino, salumi from heritage-breed pigs raised on the property. These meals, taken under pergolas overlooking the vineyards, are among the most memorable dining experiences Tuscany offers.

Guests return to the Relais in time for aperitivo in Il Salotto del Capriccio, where our sommelier is happy to continue the conversation — and to pour a glass of the very estate you visited that morning.