Wine country · CHIANTI WINE TOURS

The 15 Best Chianti Wine Tours

23 tours  ·  from $41 a head

Chianti Classico runs between Florence and Siena and every second hill has a gate you can book through. The 15 below compare estate count, whether lunch is a plate or a meal, and how much driving you sign up for.

Florence: Chianti Wineries Tour with Wine Tasting - First winery: a closer look at small-scale production
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Florence: Chianti Wineries Tour with Wine Tasting

1.Chianti Wineries Tour with Wine Tasting

★★★★★★★★★★4.5 · 10,071 reviews · 5 - 5.5 hours · from $41Our pick

Travel from Florence to two Chianti wineries by comfortable GT bus, meet local producers, walk through vineyards, and taste three to four wines at each stop. Guides such as Ana, Alex, Martina, and John add local context, while cheese, salami, olive oil, bread, and balsamic vinegar round out the tastings.

“Both wineries were beautiful and had excellent tastings. Both also offered the option to ship wines if you decided to purchase any. Emma and the driver (sorry I forgot his name) made the trip fun and informative. Both of them handled traffic well and kept us on schedule.”

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Half day Chianti Vineyard Escape from Florence with Wine Tastings - First estate: wine, food, and the cellar
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Half day Chianti Vineyard Escape from Florence with Wine Tastings

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

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

Ride from Florence to two Chianti estates with an English-speaking guide, taste three to four wines at each, sample olive oil, cheese, and balsamic vinegar, and tour vineyards and cellars. Guides such as Alex, Lorenza, and Cecilia have led especially engaging outings, though groups can reach 43 people.

“We had a great time. Our tour guide Cecilia, was charming and informative. The two wineries were different from each other, so it was interesting. Great driver too.”

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From Florence: Private Chianti Hills Tour with Tasting - The ride from Florence into the Chianti hills
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From Florence: Private Chianti Hills Tour with Tasting

3.Private Chianti Hills Tour with Tasting

★★★★★★★★★★4.3 · 809 reviews · 6 hours

Spend six hours in Chianti with a guide and minivan, stopping at two wineries and a wine shop in Radda. Taste six local wines with olive oil, cheeses, bread, and cured meats, then stroll Radda’s lanes. Hotel pickup may be requested in central Florence.

“It was fantastic. We had a great time. The wine were great, the views, Marina and Luigi... Overall a wonderful time discovering Chianti and its wine.”

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Chianti Wineries Tour with Tuscan Lunch and San Gimignano - San Gimignano between tastings
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Chianti Wineries Tour with Tuscan Lunch and San Gimignano

4.Chianti Wineries Tour with Tuscan Lunch and San Gimignano

★★★★★★★★★★5.0 · 793 reviews · 8 hours (approx.) · from $229Top rated

Spend about eight hours visiting two Chianti wineries, tasting local wines, sharing a Tuscan lunch, and exploring San Gimignano. Guides such as Lorenzo, Daniel, Christian, and Cecilia are praised for their warmth and local stories, while the group size is capped at 16.

“Tour was excellent! Daniel the tour guide was the best, he explained everything, took pictures, played great car music & so polite. Wineries were amazing, breads, cheeses, meats, vegetables & the best pasta we ever ate, so much delicious wine & food.”

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Florence: Chianti Wine Region Vespa or Fiat Topolino Tour - Your Florence departure and minivan transfer
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Florence: Chianti Wine Region Vespa or Fiat Topolino Tour

5.Chianti Wine Region Vespa or Fiat Topolino Tour

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

Join an English-speaking guide such as Niccolo, Julia, Yo, or Heather for a 6 to 6.5-hour Chianti outing from Florence. Ride a 50cc Vespa on quiet paved roads, or choose the electric Fiat Topolino. Stop in medieval villages, visit a winery, and enjoy lunch with wine and olive oil.

“Overall, the experience was great! Riding the vespa around the countryside was great! Yhe sightseeing was absolutely incredible! The tour guides were helpful with teaching you how to safely ride the vespa, and kept you safe on the road by having one guide in the front of the pack and another at the back. You got to ride the vespa long enough to really enjoy the experience. It was also really nice being able to have a little free time in Greve to shop around and enjoy a little break! That was an unexpected surprise! The wine tasting olive oil tasting and lunch was really nice! The lunch was simple,…”

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Chianti Delights: A Tale Of Two Wineries With A Vineyard Dinner - Two hours in Siena, with freedom and a catch
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Chianti Delights: A Tale Of Two Wineries With A Vineyard Dinner

6.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 and the Chianti hills. You’ll have free time in Siena, visit wine estates, taste Tuscan wines and olive oil, and enjoy a four-course dinner. Guides such as Ana, Lisa, Frederick, Diego, and Marti have led departures, though the exact guide varies.

“Very disappointed with the tour. Maybe I should have booked a different one. The tour guide was very nice, but didn’t have to do much. She led us from the bus into Siena, and then told us to meet back in 2 hours. The wine experience was poor at best. The staff showed a total lack of interest - didn’t walk us thru the meals and wine. Very little commentary from them. They missed a great opportunity as their place is beautiful. But the execution was awful. I’ve had great luck with Viator but this one was clearly the worst.”

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Chianti Vineyards Escape from Florence with Two Wine Tastings - First estate: vineyards, cellars, and a taste of rural Tuscany
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Chianti Vineyards Escape from Florence with Two Wine Tastings

7.Chianti Vineyards Escape from Florence with Two Wine Tastings

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

Leave Florence by coach for two Chianti estates, where you’ll tour cellars, see vineyards and olive groves, and taste several wines with cheese, salami, olive oil, and balsamic vinegar. Guides such as Anna, Emma, and Margherita have added warmth and useful local tips, but the group can reach 43 people.

“We liked that round-trip transportation was included in the cost. We visited two wineries for about 30-40 min each. We enjoyed Il Molino de Grace. The views at Riseccoli were nice and rustic, but we didn't like their wines very much for various reasons but mostly because the flavors were off - didn't think the grapes they used blended well together. I would say this was an efficient wine tasting with a brief opportunity to take photos. Lunch was not included. If you're looking for a slow-paced, relaxed winery visit it would probably be best to try a full day tour. Anna was our guide and she was very engaging…”

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Super Chianti 2 wineries & meat feast @ Dario Cecchini—max 8 pp - The Dario Cecchini stop and the meat feast
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Super Chianti 2 wineries & meat feast @ Dario Cecchini—max 8 pp

8.Super Chianti 2 wineries & meat feast @ Dario Cecchini—max 8 pp

★★★★★★★★★★5.0 · 258 reviews · 7 hours (approx.) · from $332

Travel from Florence in a group of no more than eight for visits to two active Chianti wineries, about 10 wine samples, and lunch at Dario Cecchini’s famous butcher shop. Guides such as Matteo, Quentin, and Clemente bring wine, food, and Tuscan culture to life.

“I have done many wine tours- most amazing but this topped them! Matteo’s passion and level of expertise is unmatched- I learned so much about how climate soil wine maker are interwoven with culture food and history and create an atmosphere that influences taste and experience. Knowing Dario’s advocacy and life story elevated our meal and quite frankly I was star struck . The van was comfortable and we bonded immediately not only with Mateo who asked us a few questions at the start that were ice breakers for our small group of 5 to connect- clever!!! The vineyards were local small owners not large producers and the cheese also…”

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Florence: Chianti Vineyards Tour with Wine Tasting & Dinner - Tasting Chianti with local food
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Florence: Chianti Vineyards Tour with Wine Tasting & Dinner

9.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 local wines and farm products, then share a candlelit dinner among the vines. Hosts such as Aurora, Marta, and Luca add local stories, while bad-weather dinners move indoors.

“Had a wonderful evening. Tour included a short stop in a beautiful town before heading to the winery. Lovely dinner in outside at a beautifully set table with a tasting of wine with each course.”

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From Florence: Wine Tasting and Dinner in Chianti Vineyards - Finding the Piazzale Montelungo meeting point
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From Florence: Wine Tasting and Dinner in Chianti Vineyards

10.Wine Tasting and Dinner in Chianti Vineyards

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

Leave Florence with an English-speaking guide for two Chianti winery visits, estate tours, tastings, and a generous Tuscan dinner paired with estate wines. You may also stop in Greve. Guides such as Chiara, Filippa, Anna, and Gabriel have led recent departures.

“It was amazing. the fact that we were by bus made it great to just drink without being afraid to drive after. The only thing is the guide rushed a little bit right after we got the last glass of wine at the last vineyard, so we didn't have time to enjoy it as mich as the other wines before. I would still redo the activity if I come back to Italy”

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Tour and Tasting at an Organic Winery in the Heart of Chianti Classico Area - Inside the cellar, where grapes become Chianti
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Tour and Tasting at an Organic Winery in the Heart of Chianti Classico Area

11.Tour and Tasting at an Organic Winery in the Heart of Chianti Classico Area

★★★★★★★★★★5.0 · 132 reviews · 2 hours (approx.) · from $48

At Fattoria di Montemaggio, Francesco leads you through organic vineyards and the cellar before tasting five or more wines with cheese, salami, bread, and estate olive oil. The small-group visit lasts about two hours, but allow extra time for the rough rural road to this remote Chianti setting.

“Fantastico! I had a wonderful morning in the beautiful montemaggio vineyard. I was the only guest but the manager still gave me a full and informative tour. The tasting session was also very professional. Would definitely take my friends there again in the future.”

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Experience Chianti & Cheese w/ 3 wineries & dairy visit—max 8 pp - The dairy visit brings cheese into the picture
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Experience Chianti & Cheese w/ 3 wineries & dairy visit—max 8 pp

12.Experience Chianti & Cheese w/ 3 wineries & dairy visit—max 8 pp

★★★★★★★★★★5.0 · 128 reviews · 7 hours (approx.) · from $338

Meet your guide at Grape Tours in Florence for a seven-hour Chianti outing limited to eight people. Visit three wineries, sample organic wines, tour a dairy, enjoy a Tuscan lunch, and return by van. The small group makes questions and personal guidance much easier.

“The day was one of our best in Italy. The driver /guide was great and the wine and cheese tastings delicious.”

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Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region - The Chianti Road: Views, Villages, and Photo Stops
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Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region

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

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

Travel by private Mercedes from Florence with a professional driver such as Placido or Christian, then explore Siena, San Gimignano, and the Chianti hills at your own pace. You can add a winery visit, tasting, and farmhouse lunch, but allow extra time if historic towns matter most to you.

“We had a very experienced driver and he was nice. A little challenging to communicate with and understand. We really enjoyed our day however we felt it was pretty rushed and would have liked to spent more time at our stops. Since we were going from Florence to Panzano next time, we will probably go a different route and save a little money and have more time.”

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Vespa Tour with Lunch&Chianti Winery from Siena - The driving test is the most important part
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Vespa Tour with Lunch&Chianti Winery from Siena

14.Vespa Tour with Lunch&Chianti Winery from Siena

★★★★★★★★★★4.0 · 126 reviews · from $168

Ride a Vespa through Chianti’s vineyard roads, stopping in Castellina, Radda, and Monteriggioni before a winery visit with wine tasting and a light lunch. You may drive your own scooter, but you must pass a safety test, hold an international driving permit, and have real Vespa experience.

“They didn’t show up even though I had a confirmation with our hotel as pick up point and didn’t refund our 600.00!”

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Greve in Chianti Wine Tasting and Winery Tour - What you learn among the vines
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Greve in Chianti Wine Tasting and Winery Tour

15.Greve in Chianti Wine Tasting and Winery Tour

★★★★★★★★★★4.5 · 119 reviews · 1 hour 30 minutes (approx.) · from $60

At Azienda Agricola Brogioni Maurizio near Greve, Maurizio or his small team introduces you to Chianti Classico, the vineyards, olive oil, and cellar. You’ll taste four red wines with cheese and Tuscan salami in a small group, with broad views over the vines and olive groves.

“It probably would have been rated higher but the two things that left a negative feel were, firstly when in booked it via Viator I was not provided a time just a day, so I had to follow up with the winery to arrange a time. On attending although it had Ben very hot all week and that morning it rained heavily at our time which understandably meant the tour of the vineyard was cancelled . What really ruined it though was we were sat on a table with a different group who had finished all their tastings but remained through ours and one of the males was nothing short…”

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New in Chianti Wine Tours

★ 5.0Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from FlorenceFrom $41310 reviews
★ 5.0Hiking Tuscany & Chianti Wine – 3 Organic Wineries with lunchFrom $23627 reviews

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