Chianti is the hill country stretching roughly between Florence and Siena, defined by vineyards, olive groves, cypress-lined roads, and the stone hill towns scattered through it — Greve in Chianti, Radda, Castellina, Panzano. It's the classic Tuscan-postcard landscape, and its wine (Chianti Classico, marked with the black rooster seal) is one of Italy's best-known reds.
How to do it: three approaches
- Organised wine tour — the simplest option: a driver, a planned route through two or three wineries, and no logistics to manage. The obvious answer if driving and tasting don't mix for your group, or if you don't want to navigate rural Tuscan roads yourself.
- Rent a car and drive yourself — gives you full control of pace and route, best suited to non-drinkers in the group or a plan built around scenery and towns rather than serious tasting. Note the region's roads are narrow and winding, genuinely enjoyable to drive but not to be underestimated.
- Private driver or small-group tour — a middle ground: a fixed vehicle and driver, but a more flexible, personalised route than a large coach tour.
What a winery visit typically involves
Most Chianti wineries welcoming day-trip visitors offer a cellar tour followed by a guided tasting of three to five wines, often paired with local snacks (bread, olive oil, cured meats, pecorino). Many require advance booking, especially smaller family-run estates — a good travel agent or tour operator will have existing relationships that make walk-in visits unnecessary.
Combining Chianti with a town stop
A full day often pairs one or two wineries with a stop in a hill town — Greve in Chianti's triangular main piazza or Radda's compact medieval centre both work well, or extend the day to San Gimignano or Siena if you're covering more ground. See our Siena guide and San Gimignano guide.