Chianti Wine Tours from Florence: The 15 Best Estate Days

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

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

Escape Florence for five hours of Chianti views, two wineries, Tuscan wines, olive oil, cheese, and a comfortable guided bus ride.

“It is a VERY big tour group - like 40-50 people (fills up a large tour bus), so it is quite hard to feel very engaged / involved. The winery tours were also quite high level, so I didn’t feel like I learnt a lot about the Chianti wine region. We tasted 3 wines at each of the 2 wineries - all of bottles were generally under €25 so not very good quality wines. The timing of starting at 2.30pm in the winter is also a pity as it gets all dark after the first wine tour and you can’t enjoy the beautiful Tuscan scenery. We knew this would happen…”

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2.Chianti Wine Region Vespa or Fiat Topolino Tour

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

Ride a Vespa or Fiat Topolino through Chianti, visit a winery, taste wine and olive oil, and enjoy a Tuscan meal from Florence.

“Amazing time! Jack, Yo & Lorenzo were amazing & made the experience super fun! Met a lot of great people while on my tour & had a delicious lunch”

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

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

Review of a Siena and Chianti evening from Florence with two wineries, Tuscan dinner, wine tastings, coach transport, and practical tips.

“Siena was really nice to see, a very unusual city. Enough time to Rome around. Wine tasting and dinner were very nice and relaxed.”

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4.Chianti Vineyards Escape from Florence with Two Wine Tastings

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

Review of a half-day Chianti wine tour from Florence, with two estate visits, tastings, Tuscan food, scenic views, and practical tips.

“Great half day wine experience. Easy to find meeting place. Wineries were beautiful and tour bus was very comfortable. Would recommend for a half day of wine tasting outside Florence.”

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5.Chianti Vineyards Tour with Wine Tasting & Dinner

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

Review of Florence’s Chianti vineyard tour with wine tasting, Tuscan dinner, countryside views, transport, value, and practical tips.

“100% recommend this experience, the guide was so knowledgable and they took us to a winery where we learn about the local wine and production with an aperitif and then the wine tasting in the vineyard with the food was incredible! I can’t recommend it enough!”

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6.Wine Tasting and Dinner in Chianti Vineyards

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

Review of Florence’s Chianti wine and dinner tour, with two wineries, Tuscan food, wine pairings, village time, costs, and practical tips.

“Was really nice. Great vineyards and we were welcomed well! The vineyard where we got the dinner was beautiful and the whole experience was much appreciated!”

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

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

Explore Siena, San Gimignano, and Chianti by private Mercedes from Florence, with flexible stops, hotel pickup, and optional winery tasting.

“Our driver Placido was wonderful. He was well versed in Tuscan history. Our tour was individualized for us, and not rushed. We were able to see everything we wanted. Placido was the perfect guide for this tour, we will definitely be requesting him again.”

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

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

Review of Siena’s Chianti vineyard dinner, with sunset wine, Tuscan dishes, transport details, value, tips, and who should book.

“I really enjoyed this activity - the only things I would suggest would be to describe the wines a little more in detail during the dinner and have some additional (non tasting) wine options to drinks. This is a gorgeous vineyard with really helpful staff.”

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9.Chianti: Vineyard to Bottle Winery Visit with Tastings

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

Review of Casa Sola Winery in Chianti, with vineyard walks, cellar tour, four wines, olive oil tasting, and practical booking advice.

“Beautiful Casa and views of the Chianti region The winery was beautiful, guide was friendly and informative, and the wine was delicious”

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

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

Review of Florence’s private Chianti half-day tour, with scenic drives, Greve, optional wine tasting, private Mercedes transport, and value advice.

“We absolutely loved this trip! Our driver was phenomenal and very helpful in knowing the area and taking us to some great places off the beaten path. Our wine tour that we set up as part of our day was easily mixed into the itinerary and helped to make the whole experience wonderful!”

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

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

Taste Chianti wines, Tuscan specialties, and a vineyard dinner on a six-hour evening tour from Florence.

“Both wineries were awesome!! Beautiful, very accommodating, and the wine is amazing!!!! The town we spent time in the small town was very peaceful and pleasing!! Our guide Gennora was the absolute best!!!!”

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

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

Review of a private Florence day trip to Siena and Chianti, with a winery visit, tasting, flexible schedule, and door-to-door transport.

“Donatello was a fantastic guide throughout our Tuscan journey. He was informative and brought us to some beautiful spots off the beaten path. We loved the entire day!”

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

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

Review of a Chianti vineyard dinner from Florence, with coach transport, estate tour, wine tasting, Tuscan food, costs, and practical tips.

“I was very disappointed that it was not held outside! Said it had rained and it hadn’t and not did it. Our host was nice but it was all very rushed and at the end of the evening we were rushed out! It included no outdoor even photo opportunity!”

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

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

Explore Chianti from Florence with a private Mercedes, flexible stops, hill towns, scenic roads, and an optional winery lunch.

“Well worth the money. Private car for the three of us. The driver has 21 years experience. He made it fun and educational. Small winery, made us feel special. Amazing day!!”

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

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

Review of a small-group Chianti Classico and Brunello tour from Siena, with boutique wineries, Tuscan food, Montalcino, and practical tips.

“Such a great experience. We started out in beautiful Siena with our host Morad. I can not say enough, Morad was so knowledgeable and answered any questions that we had. The tour was above and beyond of what we expected with great wine from Lorano winery.”

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