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Italy planning guidePlanning a wine day in Chianti from Florence

Oct 15, 2026, 5 min read, by Exclusive World Tours

This guide is for you if you are staying in Florence and want a day in the wine country to the south. It helps you choose the month, understand what you are tasting, and decide what to settle with the wineries and with your group before the day.

What Chianti Classico is

Chianti Classico is a defined wine zone between Florence and Siena. It covers about 71,800 hectares, shared between the provinces of Florence and Siena. It takes in the whole of four municipalities, Castellina, Gaiole, Greve and Radda in Chianti, and parts of four others.

The black rooster on the neck of a bottle is the emblem of the Chianti Classico consortium, founded in 1924 in Radda. When you see it at a tasting, you are drinking wine from the zone you have just driven through. Look for the same rooster if you want to find these wines at home.

When to go

Chianti works in every season, but two periods change the feel of the day.

The harvest runs from the first half of September to the second half of October. The exact days vary from estate to estate, depending on where the vineyards sit and how high they are. If you visit then, the cellars are working at full speed. You may see grapes coming in. You may also find the people pouring your wine busier than usual, so a booked visit counts for more.

The second is Expo Chianti Classico, a wine fair held in Piazza Matteotti in Greve on the second weekend of September. Producers from across the zone pour their wines in the square, and the town is full. Our stop in Greve is early in the morning, but if your date falls on that weekend, expect a fuller town and plan any time there around it.

Whatever the month, check what is happening in the villages on your date. Events change from year to year.

How the day fits together

The route follows the Chiantigiana, the old road south from Florence through the middle of the Classico zone. You are collected at 07:00 and back by 15:00. The day has three parts:

  • Two villages in the early morning. Greve, built around its triangular piazza with arcades along the sides, and then Panzano, a hill village known for its butcher and its views. The butcher's shop there is famous for bistecca alla fiorentina, the Florentine steak.
  • The first winery at 10:00. A family estate, a walk through the cellar and a tasting where the wine is made.
  • Castellina and lunch from midday, then the second winery at 13:15. Castellina has a vaulted walkway running inside its walls, the Via delle Volte, and an old fortress above it. The second estate makes wine in a different style from the first, so you can compare them.

The car is yours, so the order and the length of each stop can change on the day. If the first tasting runs long, the driver adjusts the rest.

Driving yourself, or with a driver

You can hire a car in Florence and drive the Chiantigiana yourself. The road is the easy part. The hard part is that one of you is then the driver all day, through two tastings and a lunch. On a wine day that is a real cost.

The other cost is arrangement. Visiting family estates means agreeing a time with each one, and two in a day means fitting both around lunch and the road. On this tour the winery visits are arranged for you. With a driver, everyone tastes and nobody has to think about the road back to Florence. The price depends on the size of your group; see it on the tour page.

What to book, bring and budget for

The vehicle, the driver, fuel, parking and the winery arrangements are part of the tour. The wine is not.

  • Tastings are paid at each estate. The cost varies with the wines you choose, so decide as a group whether you want the simplest tasting or the reserve wines.
  • Lunch is not included. It is meant to be the slow part of the day. Bring a card or cash for it.
  • Space in your luggage, or an address. Many estates ship wine abroad. Ask at the cellar about delivery to your country before you buy more than you can carry.
  • Something to eat at breakfast. The first tasting is at 10:00.
  • Comfortable shoes. You are on your feet in three villages and two cellars.

Who it suits, and who should think twice

It suits couples and groups of friends who like wine, and anyone who wants to see Tuscany outside the cities. You do not have to drink. The villages and the road are worth the day for their own sake, and a non-drinker in the group will not be bored.

Think twice in these cases:

  • You want the famous towns. Siena and San Gimignano are not on this route. Our Siena and San Gimignano day trip sees both and still comes home through Chianti, with a winery lunch on the way.
  • You are travelling with young children. The day is built around cellars and a long lunch. Talk to us about the pace before you book.
  • You are more than 16. Two vehicles travel together on one booking. Message us with your numbers.

Our guide to day trips from Florence compares the two days side by side.

Questions people ask

Can we choose the wineries?

The visits are arranged for you, at two estates in different styles.

Can we see Siena as well?

Yes, but on a longer day. The Siena and San Gimignano tour covers it and returns through Chianti.

Can we cancel?

Yes. Cancel up to 24 hours before pick-up and you get a full refund. See our cancellation page.

Booking the day

Choose your month with the harvest in mind, agree on a tasting budget with your group, and leave room in your bag or ask about shipping. The rest is on the Chianti wine tour from Florence page, where you choose the size of your group and book.

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