Chianti is the gently rolling wine country between Siena and Florence, a landscape of vineyards, olive trees and castles that is among the most visited parts of Tuscany. The wine that carries its name, Chianti Classico, is the reason most visitors come. This small-group day trip from Siena is a popular way to do it without driving. It runs for about eight hours in a minivan with a maximum of eight travellers, and a guide leads the day in English. Stops include Castello di Brolio, with entry included, the medieval fortified village of Castello di Vertine, and Castello di Ama, where the day includes a walk through the village, a Tuscan lunch and a wine tasting.
What the day includes
A professional guide, lunch, a wine tasting, an air-conditioned vehicle, hotel pickup and drop-off and entry to Castello di Brolio, where there is about fifty minutes to see the castle and the vineyards. The stop at Castello di Vertine is about thirty minutes and free of charge, in a former fortified medieval village. The trip meets at Piazza San Domenico in Siena, at the steps of the San Domenico basilica, and returns to the same spot.
Practical notes
The tour is not wheelchair accessible, though strollers are accepted. Alcohol is not served to anyone under eighteen. Free cancellation is offered up to 24 hours before the start. Because small tours can be merged or changed if too few travellers book, confirm your booking close to the date, particularly outside the busy months.
Choosing between tours and driving
A tour removes the problem of drinking and driving, and a guide gives context on the Chianti Classico appellation, the black rooster emblem and the history of the castles. If you prefer your own pace, hire a driver or take a day to drive the winding Chianti road with a booked tasting at one estate. Either way, spring and autumn bring the best colours, and November can be foggy and cool in the mornings.
What to expect
The experience
A guided minivan day trip in a small group of up to eight, with castle stops, a walk through a medieval village, a Tuscan lunch and a wine tasting.
Best time
Choose a clear day, since the hills are at their best in good light, and book ahead during the busy months.
How long
The tour runs about eight hours from the meeting point in Siena.
Tips
Wear comfortable shoes for the castle grounds, bring a layer, eat a light breakfast and confirm the tour a day or two before.
Quick picks
- Best for
- Wine lovers and first-time visitors who want the Chianti landscape without driving.
- Families
- Older children can join, though tastings are for adults and the day is long.
- Couples
- A small group with a long lunch makes a relaxed and romantic day out.
- Pair with
- San Gimignano and a night in Siena.
- Time needed
- A full day.
Good questions
Where does the Chianti tour start and end?+
It meets at Piazza San Domenico in Siena, at the steps of the San Domenico basilica. It returns to the same place at the end of the day.
How long is the tour and how big is the group?+
It lasts about eight hours, with a maximum of eight travellers in a minivan. The guide speaks English.
What is included?+
A guide, lunch, a wine tasting, an air-conditioned vehicle, hotel pickup and drop-off and entry to Castello di Brolio. The stop at Castello di Vertine is free.
Is the tour wheelchair accessible?+
No, it is not wheelchair accessible, though strollers are accepted. Contact the operator about specific needs.
Can I cancel?+
Free cancellation is offered up to 24 hours before the start. Small tours can be changed if too few travellers book, so confirm close to the date.







