Chianti is the honest wine day from Firenze. Two wineries, one long lunch at a fattoria, cypress-lined roads between Greve and Radda. Small-group guided tours are the sensible booking (12 to 16 people, English guide), private tours cost double, hire cars work if you have driven Italian rural roads before. September and October are peak, May and June are calm, August is hot and the wineries reduce hours around Ferragosto.
How to book, ranked
Small-group guided tour
Pickup at Piazza della Stazione or a central hotel, two wineries plus lunch, back in Firenze by 6pm. Verdict: the sensible default for first-time visitors. Price band €95 to €160 a head.
Private driver plus winery bookings
You choose the wineries, a driver handles the logistics, 8 to 10 hours door to door. Verdict: worth the premium in a group of four. Price band €480 to €820 for the car.
Hire car (self-drive)
Best flexibility, cheapest per head, requires a designated driver and comfort with Italian rural roads. Verdict: works for return visitors only. Price band €80 to €140 for the car plus €40 to €80 per tasting.
Practical tips
- Ask which wineries the tour visits. Castello di Verrazzano and Castello di Ama are honest, generic “Chianti Classico region” language is not.
- Lunch is the point, not the tasting. Book a tour that includes a fattoria meal rather than a light plate.
- Bring water and a hat between June and September. The vineyards are exposed.