Chianti is the hill country between Florence and Siena, and its heart is the Chianti Classico zone: about 71,800 hectares across Greve, Castellina, Radda and Gaiole and parts of four other comuni, the area entitled to the Black Rooster seal on its wine. It is a landscape of vineyards and olive groves broken by woods, castles and stone villages, joined by one main road, the Chiantigiana, and a web of white gravel lanes.
The north, around Greve and Panzano, is closest to Florence and busiest. Castellina sits on the ridge to the south-west, Radda and the walled hamlet of Volpaia in the middle, and Gaiole and Brolio Castle to the south-east, nearer Siena. Most visits mix wineries with village squares and long lunches, and almost all of them need a car or a tour.
About 69 kilometres of road from Florence to Siena through the middle of Chianti, with vineyards falling away on both sides.
What it is
The SR222, known as the Chiantigiana, is the road that runs through the middle of Chianti: about 69 kilometres from Florence to Siena by way of Greve, Panzano and Castellina, with the vineyards falling away on both sides. Driven straight it takes little more than an hour; with stops it fills a day.
How to do it
Leave Florence early, stop in Greve for its arcaded square, climb to Panzano for the view over the Conca d'Oro valley, and from Castellina either continue to Siena or turn left for Radda and Gaiole. From Greve, a narrow, partly unpaved road leads west past the hamlet of Montefioralle to the abbey of Badia a Passignano.
Good to know
If you will be tasting, take a tour or a driver; the bus, line 365, reaches Greve, Panzano, Radda and Gaiole but not the wineries.
Taste Chianti Classico by its three levels, Black Rooster in hand
Wineries across the Chianti Classico zone
1 and a half to 2 hours per wineryBook ahead
Taste your way up the three levels of Chianti Classico, the wine with the Black Rooster on the neck of the bottle.
What it is
Look for the Black Rooster on the neck of the bottle: it marks Chianti Classico, a separate DOCG from plain Chianti, made only in the historic zone, from at least 80 per cent Sangiovese and, since 2006, only red grapes. The rooster was the emblem of the medieval Chianti League, and the growers' consortium that adopted it was founded in Radda on 14 May 1924.
How to do it
A good tasting runs up the three levels: Annata, aged at least 12 months; Riserva, at least 24; and Gran Selezione, at least 30 months, from at least 90 per cent Sangiovese and only the estate's own grapes. The consortium's Chianti Classico Card lists over 100 wineries and their experiences.
Good to know
Most wineries take visitors by reservation for a cellar tour and tasting, so book a day or more ahead.
Visit Brolio Castle, where the Chianti recipe was written
Brolio, Gaiole in Chianti
2 hours with a tastingBook ahead
The Ricasoli castle on a ridge above Gaiole, where a baron worked out the blend that became the model for Chianti.
What it is
Brolio, recorded since 1141, is the castle of the Ricasoli family on a ridge above Gaiole, at the southern end of Chianti, and its estate of 1,200 hectares still has 240 hectares of vines. In the 19th century Baron Bettino Ricasoli, later prime minister of Italy, experimented here with the blend that became the model for Chianti: Sangiovese, softened with Canaiolo and a little white Malvasia.
How to do it
The visit covers the gardens, the chapel of San Jacopo with the family crypt and the walls with their view over the vineyards towards Siena, and the estate's wine shop below runs tastings.
Good to know
From 25 October to 20 December 2026 the castle opens daily 10:00 to 17:00, with the ticket office closing at 16:00; it is closed from January to mid March.
Shop Greve's arcaded square and the Falorni butcher's
Piazza Matteotti, Greve in Chianti
1 to 2 hoursNo booking needed
An arcaded triangle of a square, and under its arches a butcher's run by the same family since 1806, selling fennel salami.
What it is
Greve's Piazza Matteotti is a long triangle lined with arcades, with a statue of Giovanni da Verrazzano, born nearby in 1485, the navigator who sailed into New York Bay in 1524, in the middle. On Saturday mornings the market fills it, and it also hosts the Expo Chianti Classico wine fair. Under the arcades at number 66 is the Antica Macelleria Falorni, a butcher's run by the same family since 1806, when Lorenzo Falorni turned the family inn into a shop.
How to do it
Buy finocchiona, the fennel salami, wild boar salami and prosciutto to take away, or sit down in its bistro for a tasting plate. Then walk up the lane to Montefioralle, a ring-shaped medieval hamlet on the hill above.
Good to know
The shop opens every day, from 9:00 Monday to Saturday and from 10:00 on Sundays, until 19:30.
The butcher's counter where Chianti goes for meat, with spiced lard, raw beef sushi del Chianti and steak menus upstairs.
What it is
Dario Cecchini has worked behind the counter of the Antica Macelleria Cecchini in Panzano for more than 50 years, and his shop on Via XX Luglio is where Chianti goes for meat. Come in for his finocchiona, the spiced lard he calls burro del Chianti or the raw beef sushi del Chianti. Upstairs, Solociccia serves a set menu of €50 at one sitting a day, at 12:00, with a vegetarian version, and the Officina della Bistecca grills steaks for a set menu of €50 at lunch and dinner.
How to do it
The shop opens every day from 9:00 to 16:00, except Christmas Day. Both restaurants run every day; ask for a table through the booking form on his site.
Good to know
If you want a large Florentine steak to take away, order it a day ahead.
See Ghirlandaio's first Last Supper at Badia a Passignano
Badia a Passignano, Tavarnelle
1 hour for the abbey, more with the cellarTimed entry
A towered abbey rising out of the vineyards, with Ghirlandaio's first Last Supper in its refectory, painted in the summer of 1476.
What it is
The Vallombrosan abbey of Badia a Passignano rises with its towers out of the vineyards west of Greve. Saint John Gualbert, the order's founder, died here in 1073 and is buried in the church, and Galileo later taught mathematics to the monks. In the refectory is the Last Supper that Domenico Ghirlandaio painted with his brother Davide in the summer of 1476, his first, years before the better-known versions in Florence.
How to do it
The abbey is seen only on guided visits, which must be booked by WhatsApp or email: every day except Tuesday, with tours in Italian at 10:00, 11:30, 15:00 and 16:15 and in English at 10:15, 11:30, 15:15 and 16:30 from Monday to Saturday, and in the afternoon on Sundays.
Good to know
The surrounding vineyards belong to Antinori, whose cellar under the abbey runs its own tastings, also by reservation.
Walk Castellina's covered street and its Etruscan tomb
Castellina in Chianti
2 hoursNo booking needed
A long vaulted passage inside the walls with openings onto the countryside, a fortress tower to climb and an Etruscan burial mound.
What it is
Castellina sits on the ridge between the Elsa, Pesa and Arbia valleys, and its old defences survive in two places. Via delle Volte is the covered walkway built along the inside of the walls, a long vaulted passage with openings onto the countryside. The 15th-century Rocca on Piazza del Comune now holds the Museo Archeologico del Chianti Senese, with finds from the Etruscan tombs around the village and a reconstruction of a parade chariot. Just north of the village rises the Montecalvario tumulus, an Etruscan burial mound about 50 metres across, excavated in the early 20th century.
How to do it
The museum ticket includes the climb up the tower for the view. It opens daily 10:00 to 13:30 and 14:00 to 18:00, and a full ticket costs €9.
Good to know
Castellina is also the crossroads where the Chiantigiana meets the road to Radda.
Ride white gravel roads of Chianti on the permanent Eroica route, all year and on any bike, or join thousands in wool jerseys each October.
What it is
L'Eroica began in Gaiole in 1997 as a ride for vintage racing bicycles on the white gravel roads of Chianti, and it now draws thousands of riders in wool jerseys each October; in 2026 it ran on 3 and 4 October, with routes from 45 to about 210 kilometres. The event needs a bicycle built in 1987 or earlier.
How to do it
You do not have to wait for it: the permanent Eroica route, a loop of a little over 200 kilometres from Gaiole through Chianti and the Crete Senesi towards Montalcino, can be ridden all year on any bike, and the organisers publish the GPX track on their site. Most riders do a section rather than the whole loop.
Good to know
Gravel or wide tyres help on the strade bianche, and the climbs out of Gaiole are steep, so start early.
Taste wine inside the walls of Volpaia above Radda
Volpaia, Radda in Chianti
Half a day with RaddaBook ahead
A stone hamlet above 600 metres, among Chianti's highest villages, with cellars hidden inside its old houses and walls.
What it is
Volpaia is a fortified hamlet of Radda at more than 600 metres, among the highest villages in Chianti, recorded since 1172 and still almost entirely stone. Its main square is overlooked by the castle tower, and a small Renaissance church of the mid 1400s, the Commenda di Sant'Eufrosino, stands just below. The village is also a winery: Castello di Volpaia keeps its cellars hidden inside the old houses and walls, with vineyards above 400 metres.
How to do it
Walking paths leave from the village into the woods. Then drive the few kilometres down to Radda, the small walled town where the Chianti Classico growers founded their consortium in 1924, for a walk round its ring of streets and dinner.
Good to know
Castello di Volpaia runs visits and tastings by booking through its site.
The SR222, the Chiantigiana, runs about 69 kilometres from Florence to Siena through Greve, Panzano and Castellina, so the area starts within an hour of either city. Without a car, Autolinee Toscane's line 365 links Florence with Greve, continuing to Panzano or to Radda and Gaiole, but services are not frequent.
Getting around
By car, or with a driver if you plan to taste seriously: the wineries are spread out, often down gravel roads, and the bus does not reach most of them. Village centres are small; park at the edge and walk in. Cycling is popular on the quiet roads, but the hills are steep.
How many days
In must30's view, two or three nights. One day for Greve, Montefioralle, Panzano and Badia a Passignano in the north, and one for Radda, Volpaia, Gaiole and Brolio further south, with a winery visit each day. A single day trip from Florence works if you keep to the north.
When to go
September and October bring the harvest and the busiest wine calendar; Panzano holds Vino al Vino on the third weekend of September. Spring is green and quieter. Some estates, Brolio among them, close their visits in winter, so check before a trip between January and March.
Where to base yourself
Greve and Panzano for the north and the shortest drive from Florence, with the most restaurants; Radda or Castellina for a central base; Gaiole for the south and Brolio. Many visitors stay on a wine estate or farm in between, which means driving to every meal.
Questions travellers ask
What is the difference between Chianti and Chianti Classico?
Chianti Classico is a separate DOCG made only in the historic zone between Florence and Siena, with at least 80 per cent Sangiovese and the Black Rooster seal on the bottle. Plain Chianti comes from a much larger area around it, under different rules.
Do you need to book winery visits in Chianti?
Yes, in practice. Most estates run tours and tastings at set times by reservation, and some, such as Antinori at Badia a Passignano, only by reservation. The consortium's Chianti Classico Card lists more than 100 wineries and their experiences.
Can you visit Chianti without a car?
Partly. The 365 bus reaches Greve, Panzano, Radda and Gaiole from Florence, but most wineries are out of reach on foot. A guided wine tour from Florence or Siena, or a hired driver, is the easier option if you want to taste.
Which Chianti village should I see if I only have one day?
Greve and Panzano, which sit close together on the Chiantigiana within an hour of Florence. Greve has the arcaded square and Falorni's butcher's shop, Panzano has Dario Cecchini and the views, and Badia a Passignano is a short detour.
