The Best Chianti Wine Tours from Florence: Five We Would Book

The short version: if you want the wine, book the Essence of Chianti day with three estates and lunch; if you want the day out, book the Vespa or Topolino tour; if you have an evening rather than a day, book the seven-wine tasting in town and skip the bus altogether. Below is how we got there, what each tour actually involves, and the ones we left out.

Chianti Classico starts twenty minutes south of Florence and the tours all go to roughly the same hills, so the differences are in format: how many wineries, how big the group, whether lunch is a sit-down meal or a snack, and whether you spend the day in a van, on a scooter or at a table. We compared the tours with the strongest review records on GetYourGuide and Viator and picked five.

At a glance

1. Essence of Chianti: three wineries and lunch

This is the tour to book if the wine is the point. Three family estates between Greve and Castellina, each showing a different level of Chianti Classico, from the annata through Riserva to Gran Selezione, with a proper seated lunch at the second estate and a stop in Greve, the region’s market town. The group is capped at eight, which is why it costs more than the coach tours, and the reviews, more than a thousand of them at a high average, say the money is well spent. Six and a half hours from central Florence. Check dates and book.

2. Chianti by Vespa or electric Topolino

The tour people talk about for years afterwards. You ride a Vespa, or drive a tiny electric Fiat Topolino if you would rather not, in convoy along the back roads south of Florence, stop at the lookouts the buses cannot reach, and sit down to lunch at a villa before a cellar visit and tasting. One winery rather than three, but a far better day. Vespa riders need a driving licence and some confidence; the Topolino is the gentler choice. Runs April to October. Check dates and book.

3. Seven Tuscan wines in a Florence tasting room

Not a Chianti tour, but the right booking for a lot of people: ninety minutes in the city, seven wines that put Chianti, Chianti Classico, Vino Nobile, Brunello and a Super Tuscan side by side with a board of cheese and salumi, and no bus. A winery can only pour its own wine; this is the one format that lets you compare regions before you commit a day to one of them. Check dates and book.

4. Chianti and castles from Siena

If you are staying in Siena, do not drive to Florence for a tour; the southern Chianti is on your doorstep. This afternoon tour visits a castle estate for a cellar tour and a seven-wine tasting with olive oil and balsamic, then stops in the walled village of Monteriggioni on the way back. Eight guests maximum and about five hours. Check dates and book.

5. An estate tasting for self-drivers

With your own car, the full-day tours make no sense, but many estates only open by reservation. This one-hour booking at a historic Chianti Classico estate gives you a cellar tour and a flight of the wines with the olive oil, at a fixed time you can plan around, for the price of a bottle. Check dates and book.

What we left out, and why

Large-coach Chianti tours with fifty guests and one winery: the reviews are fine, the experience is not. Combined “Chianti, Siena, San Gimignano and Pisa in a day” tours: you will spend the day in a van and taste one wine. Private driver days: excellent if you have four people and the budget, but at two to three times the price of the small-group tours above they are not where most readers should start.

Frequently asked questions

How far is Chianti from Florence?

The Chianti Classico zone begins about 20 km south of the city; Greve in Chianti is 40 minutes by car. Tours spend one to two hours driving in total.

Can I visit Chianti from Florence without a tour?

Yes by car, with estate tastings booked in advance, and awkwardly by bus to Greve. Our guide to Tuscan wineries without a car covers the options.

When is the best time for a Chianti wine tour?

May to June and September to October. Harvest in late September is the most interesting time in the cellars. Winter tours run but some estates close.

Do the tours include lunch?

The Essence of Chianti and Vespa tours include a seated lunch; the Siena castle tour includes snacks with the tasting; the city tasting includes a board. Check each listing.

Is Chianti or Montalcino better for a day trip?

Chianti is closer, cheaper and more scenic for a half day; Montalcino is for serious red-wine drinkers with a full day. Our Chianti vs Montalcino vs Montepulciano guide goes into it.

See all options on our wine tours from Florence and Chianti pages.