Chianti Classico Black Rooster and Super Tuscan Wine Tour

Two family wineries, a homemade Tuscan lunch, and the medieval hillsides of Castellina in Chianti — all in one private day.

This Chianti Classico wine tour from Florence takes you deep into the Tuscan countryside on a private, unhurried journey through two authentic family-run estates, where winemaking is still a matter of personal pride and seasonal rhythm. Far from the crowds of mass tourism, each stop offers genuine access to the people behind the bottles.

The route follows the Via Chiantigiana, the celebrated wine road that winds through vineyards and cypress groves connecting Florence to the heart of the Chianti Classico zone. Your driver provides context along the way, touching on the history of the Black Rooster consortium and the landscape that shapes the wines you will taste.

At the second winery, the experience shifts from tasting room to family table. The mother of the estate prepares a three-course lunch using seasonal ingredients grown or sourced locally, paired with wines and the property's own extra-virgin olive oil. This is the kind of meal that does not appear on menus but endures in memory.

The afternoon visit to Castellina in Chianti rounds out the day with a walk through a medieval hilltop village that has changed little since it served as a Florentine fortification in the late 13th century. Local artisan workshops and panoramic views of the surrounding hills make it an ideal place to pause before the return to Florence.