WINE COUNTRY · CHIANTI WINE TOURS

Chianti Wine Tours from Florence: the 15 Best Half-Days

30 tours  ·  from $30 a head

Chianti Classico is forty minutes from the Duomo and half a day is enough. The 15 below sort the morning escapes, the Vespa runs and the full days with dinner, with prices, pickup points and how many estates each one reaches.

Half day Chianti Vineyard Escape from Florence with Wine Tastings - The Chianti Road and its first views
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Half day Chianti Vineyard Escape from Florence with Wine Tastings

1.Half day Chianti Vineyard Escape from Florence with Wine Tastings

★★★★★★★★★★4.5 · 2,196 reviews · 5 hours (approx.) · from $53Our pick

Ride from Florence to two Chianti estates by comfortable coach, tasting three to four wines at each with olive oil, cheese, and balsamic vinegar. Walk through vineyards, visit cellars, and hear about Tuscan winemaking from an English-speaking guide. Guides such as Alex and Lorenza have been praised for friendly, clear commentary.

“The wineries were wonderful and the tour overall was enjoyable. However, the tour guide was not very engaging and spent most of the time chatting with the driver, which made her presence feel unnecessary.”

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Florence: Chianti Wine Region Vespa or Fiat Topolino Tour - The Safety Lesson Before the Ride
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Florence: Chianti Wine Region Vespa or Fiat Topolino Tour

2.Chianti Wine Region Vespa or Fiat Topolino Tour

★★★★★★★★★★4.8 · 739 reviews · 6 - 6.5 hours

Leave Florence by minivan for a guided ride through Chianti, Impruneta, and Chiocchio. Choose a 50cc Vespa, electric Vespa, Piaggio Zip, or Fiat Topolino. Guides such as Niccolò, Julia, Heather, and Yo provide scooter training, route support, and local stories before a winery visit, Tuscan meal, and wine and olive oil tasting.

“Everything from the trip to the guides and the food was great.”

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Chianti Delights: A Tale Of Two Wineries With A Vineyard Dinner - What the winery visit really includes
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Chianti Delights: A Tale Of Two Wineries With A Vineyard Dinner

3.Chianti Delights: A Tale Of Two Wineries With A Vineyard Dinner

★★★★★★★★★★4.0 · 324 reviews · 7 hours 30 minutes (approx.) · from $106

Leave Florence at 2:45 pm for Siena, then continue through Chianti for winery visits, tastings, olive oil, and a four-course Tuscan dinner. You get a comfortable coach, an English-speaking guide, and sunset countryside views when timing and weather cooperate. Guides have included Ana, Diego, Frederick, Lisa, Marti, and Sebastian.

“Great information on the grapes in the vineyard and an excellent meal was served with the wine tasting offering a different taste for each course.”

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Chianti Vineyards Escape from Florence with Two Wine Tastings - The ride along the Chianti Wine Road
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Chianti Vineyards Escape from Florence with Two Wine Tastings

4.Chianti Vineyards Escape from Florence with Two Wine Tastings

★★★★★★★★★★4.5 · 280 reviews · 5 hours (approx.) · from $53

Leave Florence from Piazzale Montelungo for a five-hour afternoon in Chianti. An English-speaking guide leads you to two changing wine estates for cellar visits, vineyard views, several wines, olive oil, cheese, salami, and balsamic vinegar. Guides such as Emma, Anna, Margherita, and Alex have helped make past departures especially enjoyable, though the group may include up to 43 people.

“This was such an incredible experience. We got on a big bus and drove through the beautiful Tuscany landscape to visit two different vineyards. At each, we tasted two red wines and one white wine, which was accompanied with cheese, salami, and bread. We got to hear all about the history of the region and the effort it takes to make these wines. As someone who loves red wine, it was an incredible experience. It was not too much wine, just tasters of each, and the drive between the two gives you a break. There’s options to buy a glass or a bottle of any wine ant each location. I…”

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Florence: Chianti Vineyards Tour with Wine Tasting & Dinner - Leaving Florence for the Tuscan hills
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Florence: Chianti Vineyards Tour with Wine Tasting & Dinner

5.Chianti Vineyards Tour with Wine Tasting & Dinner

★★★★★★★★★★4.1 · 226 reviews · 8 hours · from $128

Travel from Florence by air-conditioned minivan or coach to a Tuscan wine estate. Tour the winery, taste several wines, then sit down to a generous farm-style dinner among the vines. Hosts such as Aurora, Marta, Luca, and Leticia have made the evening personal and informative. Dinner moves indoors if weather turns bad.

“i enjoyed learning about the making of the wine, wine tasting and dinner with others from around the world in the vineyard.”

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From Florence: Wine Tasting and Dinner in Chianti Vineyards - A first winery visit focused on how Chianti is made
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From Florence: Wine Tasting and Dinner in Chianti Vineyards

6.Wine Tasting and Dinner in Chianti Vineyards

★★★★★★★★★★4.6 · 192 reviews · 6.5 hours · from $141

Leave Florence for two Chianti wineries, with vineyard and cellar visits, wine and olive oil tastings, Tuscan snacks, and a multi-course dinner paired with estate wines. Guides such as Chiara, Phillipa, Anna, and Gabriel have led departures, though staffing changes. A short stop in Greve may be included.

“A very good choice for a different type of activity in Florence, the two vineyards visited were beautiful, with good wine selection, the dinner and wine tasting at Tenuta Torciano was one of the best we’ve had had at a vineyard, very good dinner, excellent hosts”

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Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region - San Gimignano: towers, gelato, and a short walk
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Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region

7.Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region

★★★★★★★★★★4.5 · 128 reviews · 8 hours (approx.) · from $520

Travel from Florence by private Mercedes with a driver such as Placido, Christian, Julian, or Valentine. Explore Siena and San Gimignano at your own pace, then follow the Chiantigiana wine road. Add a winery tasting and farmhouse lunch if you want. Hotel pickup, WiFi, and return transport are included.

“Wonderful guide and friend. He was the most charming gentleman who made us so comfortable. Would really recommend him.”

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From Siena/Chianti: Dinner & Drinks in the Chianti Vineyards - A farm winery and the first glass of wine
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From Siena/Chianti: Dinner & Drinks in the Chianti Vineyards

8.From Siena/Chianti: Dinner & Drinks in the Chianti Vineyards

★★★★★★★★★★4.0 · 95 reviews · from $123

From Siena, ride by air-conditioned minivan to a Chianti farm for a sunset aperitivo, winery visit, chapel stop, and candle-lit four-course dinner. Expect roast meats, grilled vegetables, dessert, wine, and water. English, Italian, and Spanish guides lead the evening, with vegetarian meals available on request.

“The tour was very well organised and our guide was excellent.”

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Chianti: Vineyard to Bottle Winery Visit with Tastings - Inside the Ancient Cellar
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Chianti: Vineyard to Bottle Winery Visit with Tastings

9.Chianti: Vineyard to Bottle Winery Visit with Tastings

★★★★★★★★★★4.8 · 71 reviews · 1.5 hours · from $37

At family-run Casa Sola Winery between Florence and Siena, you’ll walk through vineyards and olive fields, visit the ancient cellar, and sit down with a guide for three red wines, Vin Santo, Tuscan bread, olive oil, and balsamic. Andrea has guided some visits, and tours run in English, French, or Spanish.

“Estuvo excelente el tour. Andrea el guía fue muy amable y buena onda.”

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Florence: Private Half-Day Chianti Tour and Wine Tasting Optional - Adding a winery visit and tasting
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Florence: Private Half-Day Chianti Tour and Wine Tasting Optional

10.Private Half-Day Chianti Tour and Wine Tasting Optional

★★★★★★★★★★4.5 · 49 reviews · 5 hours (approx.) · from $378

Leave Florence in a private Mercedes with a driver such as Placido, Osvaldo, Cristian, or Alejandro. Ride through Chianti’s vineyards and olive groves, stop for photos, explore Greve, and add a winery visit if you wish. The five-hour plan is flexible, but wine, lunch, and guided sightseeing cost extra.

“Placido was wonderful! Ontime, clean car and very knowledgeable!!! He made the experience so enjoyable. We would absolutely book a tour with him again.”

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Exclusive Winery Tour with Tasting and Dinner in Chianti vineyard - Greve gives you an hour to slow down
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Exclusive Winery Tour with Tasting and Dinner in Chianti vineyard

11.Exclusive Winery Tour with Tasting and Dinner in Chianti vineyard

★★★★★★★★★★4.5 · 49 reviews · 6 hours 30 minutes (approx.) · from $144

Leave Florence at 3 p.m. for two Chianti wineries, a cellar lesson, tastings of wine, cured meats, olive oil, and balsamic, plus free time in Greve. Finish with a multi-course Tuscan dinner paired with local wine. Guides may include Jackie, Lucy, Nico, Stefano, or Gennora, and groups are limited to 25.

“Both wineries though completely different were great and the short time spent walking around Grève added to the trip.”

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Private daytrip to Siena & Chianti wine country, with wine tasting from Florence - Inside Fattoria di Montecchio
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Private daytrip to Siena & Chianti wine country, with wine tasting from Florence

12.Private daytrip to Siena & Chianti wine country, with wine tasting from Florence

★★★★★★★★★★5.0 · 43 reviews · 8 hours (approx.) · from $467Top rated

Spend about eight hours with a private English-speaking driver exploring Greve, Panzano, a Chianti winery, and Siena. Taste Chianti Classico, Riserva, Super Tuscan wines, and olive oil, with lunch optional. Drivers such as Mario, Donatello, Thommas, and Giuseppe have adapted routes to suit each group.

“Our driver Donatello was great! He suggested a wonderful iteneriary that allowed us to see a few places that we wanted that weren’t even part of the tour. He was so knowledgeable and personable, it really made the day. We loved Sienna. And the meal and wine tasting at Casa Emma was very good.”

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Chianti vineyards: Small-Group tour with wine tasting & Dinner - Touring the estate, cellar, and chapel
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Chianti vineyards: Small-Group tour with wine tasting & Dinner

13.Chianti vineyards: Small-Group tour with wine tasting & Dinner

★★★★★★★★★★4.0 · 38 reviews · from $126

Leave Florence for a small Chianti estate, tour the wine cellar and chapel, taste local wines, and share a four-course Tuscan dinner under candles and stars. Guides such as Simone and Marco have earned praise for warm, informative hosting. Dinner moves indoors in bad weather, and vegetarian options require advance notice.

“Marco, our tour guide to the winery, was so informative! Simone was a WONDERFUL tour guide at the winery! We got to taste as well as smell balsamic and cannot go back to store bought. We got to try truffle olive oil and homemade lasagna. The meal was wonderful and we tried 4 types of wine. I don't like wine and I found a white I really enjoy.”

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Florence: Private Full-Day Chianti Tour and Winery Lunch Optional - Three hours in Greve in Chianti
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Florence: Private Full-Day Chianti Tour and Winery Lunch Optional

14.Private Full-Day Chianti Tour and Winery Lunch Optional

★★★★★★★★★★5.0 · 31 reviews · 8 hours (approx.) · from $472

Set out from your Florence hotel with a private driver in an air-conditioned Mercedes. Shape the day around Greve in Chianti, Montefioralle, Panzano, wineries, or other Tuscan towns. Drivers such as Cristian and Placido can adjust the route, while the optional winery lunch adds tastings and local food at extra cost.

“Amazing experience, Placido was a phenomenal driver and guide. We went to some amazing wineries and just had a perfect no rush day. I would book this again and again.”

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Small group Chianti Classico & Brunello wine region from Siena - The drive from Chianti to Montalcino
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Small group Chianti Classico & Brunello wine region from Siena

15.Small group Chianti Classico & Brunello wine region from Siena

★★★★★★★★★★5.0 · 31 reviews · 5 hours 30 minutes (approx.) · from $198

Leave Siena at 2 pm for a small-group afternoon through Chianti Classico and Montalcino. With a maximum of six people, you visit a family-run organic winery, taste Chianti with pecorino, cured meats, olive oil, and balsamic vinegar, then see Montalcino or choose a second Brunello tasting. Guides such as Morad and Stephanie add local detail.

“Our driver, Murad, was exceptionally friendly and informative - he was able to share videos of Palio di Sienna during the drive. Highly recommend!!”

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