A three-day itinerary through villages, wineries and white gravel roads of the Chianti, based in Castellina, for anyone short on time but wanting to see it properly.
Three days are enough to get a real feel for the Chianti, as long as you don't try to see everything. It's best to pick a central base, such as Castellina in Chianti, and move out from there at an easy pace, alternating villages, wineries and a little unplanned time. Here's how we'd put together a three-day itinerary for anyone staying in the area.
Day 1: Castellina and the surrounding area
It's worth spending the first day getting to know the area without moving around too much. Castellina in Chianti rewards an unhurried walk: the Etruscan walkway beneath the walls, the Rocca fortress, the lanes of the historic centre. In the afternoon you could pay a first visit to a cellar, perhaps ours, to understand how Chianti Classico is produced before visiting others later in the trip. In the evening, if it's Friday or Saturday, it's the perfect time to stop for dinner with us and our house menu.
Day 2: Radda, Volpaia and the white gravel roads
The second day can be devoted to a wider loop towards the north-east, in the direction of Radda in Chianti, another fortified village worth a couple of hours' stop. From there, the road to the small village of Volpaia crosses some of the most photographed hills in the Chianti, with vineyards alternating with cypress woods. Anyone who likes to travel differently can book a guided e-bike ride along these same white gravel roads: a slower but more immersive way to take in the landscape. In the afternoon, head back to Castellina at an easy pace, perhaps stopping for an aperitivo in the square.
Day 3: Siena or Florence, and back among the vineyards
The third day is the moment to step outside the Chianti for a trip to one of the two cities that frame it. Siena, just 25 minutes' drive from Castellina, can comfortably be visited in half a day: Piazza del Campo, the Cathedral, a quick lunch in a trattoria in the centre. Florence, on the other hand, takes a full day, given the roughly 50-minute drive and the sheer number of things to see: it's best to set off early in the morning. Anyone who prefers to stay closer to home can instead devote the last day to an on-site activity, such as a guided tasting or a Tuscan cooking class, before heading off.
Practical tips
To get around the Chianti, it's best to have a car: public transport between the villages is limited, and the scenic roads are part of the experience. The white gravel roads are passable with any car, but should be driven with care, especially after rain. Booking wineries a few days in advance avoids finding closed doors, particularly on weekends in high season between May and October.
Three days aren't enough to exhaust the Chianti, but they're enough to go home with a clear idea of what this land is about: not just wine, but a way of living in the countryside that you can feel in every village you pass through.