The 15 Best Chianti Wine Tours from Florence

1.Chianti Wineries Tour with Wine Tasting

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

Ride from Florence into the Chianti Hills for two winery visits, guided tastings, vineyard walks, and samples of cheese, salami, bread, olive oil, and balsamic vinegar. Guides such as Ana, Alex, Martina, and John bring local color, while the two wineries often contrast family tradition with larger-scale production.

“Loved the two wineries we went to! They had a good variety of wines and amazing cheeses, especially the first winery! You even get to meet the goats who made the cheese! And the Tuscan countryside was beautiful. The transportation was comfortable and safe. The guide and driver were helpful and friendly. Highly recommend!”

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2.San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 4,432 reviews · 11 hours (approx.) · from $83

Travel from Florence through Chianti vineyards to San Gimignano, Monteriggioni, Siena, and a winery lunch. You get free time in the medieval towns, optional Siena guiding, and an optional skip-the-line Cathedral and Piccolomini Library visit. Guides such as Sandro, Marta, and Ilaria are often praised for clear, friendly help.

“Lovely informative day to see a slice of Tuscany. Our guides were great and the bus very comfortable. Met some lovely people also. Would recommend this tour.”

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3.Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

★★★★★★★★★★4.6 · 4,354 reviews · 12 hours · from $77

Spend 12 hours touring Tuscany from Florence, with stops at Pisa’s Square of Miracles, tower-filled San Gimignano, the Chianti Hills, and Siena. Choose the lunch and wine tasting, plus Siena’s guided walk and cathedral entry. English and Spanish guides may include Marta, Aaron, Sandro, or Federico.

“Very well organised from start to finish! Guides were brilliant, transport very comfortable, lunch was lovely and got to see some beautiful parts of Italy! A great day thank you!”

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4.Chianti Wine Tour from Florence

★★★★★★★★★★4.5 · 3,979 reviews · 5 hours (approx.) · from $59

Leave Florence by air-conditioned coach for two Chianti wineries along the Via Chiantigiana. Walk through vineyards, visit cellars, taste Tuscan wines with cheese, salami, bruschetta, olive oil, and balsamic vinegar, and return to Piazzale Montelungo after about five hours.

“That the tour guide will rush you and tell you there will be time for you to take pictures after the wine tasting and then tell you there is no time. Get on the bus . Get on the bus. She will attempt to tell you this again at the next stop but by that time you know she’s not telling the truth. My suggestto the company is that after purchasing the wine and bathroom they give 10 to 15 minutes for photo opportunities Other than that best tour I took while in Italy.”

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5.San Gimignano, Siena, and Chianti Wine Tour

★★★★★★★★★★4.5 · 3,762 reviews · from $164

Leave Florence for Siena, a Chianti estate, and San Gimignano in nine hours. You’ll taste five wines, sample olive oils, eat Tuscan specialties, and explore each town with guidance plus free time. Guides may include Marco, Lyla, Marta, or Emma.

“The guide was very informative and engaging. We had a fantastic day and got what we wanted, history, fantastic surroundings and wine yard.”

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6.S. Gimignano, Siena, Chianti Wine Tasting & Lunch

★★★★★★★★★★4.6 · 3,102 reviews · 11 hours · from $82

Travel from Florence by air-conditioned coach to San Gimignano, Siena, Monteriggioni, and a Chianti winery. Expect free time in the hill towns, a three-course Tuscan lunch, three wine tastings plus Vin Santo, and optional guided visits in Siena with guides such as Marta, Riccardo, or Sandro.

“Incredible value for what you get. Constantino was an excellent host for the day, and Alexa was so helpful and kept things running on time. Sylvio was an incredible driver- I felt very safe the whole time we were in the bus. The tour was so fun and the food at the winery was absolutely incredible. I would absolutely recommend this tour- it’s such a great way to see some of the beauty Tuscany has to offer.”

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7.Chianti Half-Day Wine Tour with Tasting

★★★★★★★★★★4.5 · 3,031 reviews · 6 hours · from $58

Leave Florence by coach for two Chianti wineries, tasting seven wines with salami, cheese, bruschetta, olive oil, and balsamic vinegar. You will also visit Monteriggioni. Guides such as Luca, Luciano, Marco, Alicia, and Leonardo have led recent departures, with time split between tastings, views, and shopping.

“Excellent wine tour. Well organised. Luca and Luciano were amazing. We really enjoyed ourselves. Even the visit to Monteriggioni was very interesting.”

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8.Siena, San Gimignano and Chianti Wines Day Tour from Florence

★★★★★★★★★★4.5 · 2,542 reviews · 10 hours 30 minutes (approx.) · from $78

Leave Florence by air-conditioned coach for Monteriggioni, Siena, San Gimignano, and a Chianti estate. You get guided highlights in Siena, free time in the hill towns, and a tasting of up to three wines with snacks. Guides such as Alex, Constantino, and Gabrielle have earned praise for clear, lively leadership.

“Such beautiful places and our guides Sara and Lorenza were great. Our bus driver Mario was very good as well.”

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

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

Leave Florence by Wi-Fi-equipped coach for two Chianti estates along the famous Chianti Road. Meet winemakers, tour vineyards and cellars, taste up to eight wines with olive oil, cheese, and balsamic vinegar, then return to Santa Maria Novella.

“It was a nice trip! The tour guide lady explained everything well, think her her is Laurence. The two farms were nice. The first tasting we were too many for the room, suggest to give it a more personal touch. The views were spectacular. We went end October and Autumn was in full bloom. It was a lovely trip.”

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10.Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

★★★★★★★★★★5.0 · 1,300 reviews · 6 hours (approx.) · from $145Top rated

Leave Florence by van for a guided ride through Chianti’s vineyards, olive groves, and winding roads. Guides such as Ben, Angus, Alessio, and Filippo lead the route, with a support van for the steepest hill. Finish at a medieval castle with wine, olive oil, and lunch.

“Angus was so friendly and knowledable. My family of 4 had a great time. The views were amazing, very worth the ride. There was a stretch at the end of the ride that was quite challenging so keep that in mind if taking young children.”

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11.Chianti Tour with Two Wine and Food Tastings

★★★★★★★★★★4.5 · 1,205 reviews · 5 hours · from $58

Travel from Florence along the Via Chiantigiana to two family-run organic wineries in Chianti Classico. Meet hosts such as Fernando and enjoy cellar visits, vineyard walks, wine, olive oil, balsamic vinegar, and Tuscan snacks. A morning cooking class with lunch and four wines is also available.

“Beautiful scenery learning & tasting numerous wines, it was a really enjoyable experience.”

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12.Private Chianti Hills Tour with Tasting

★★★★★★★★★★4.3 · 809 reviews · 6 hours

Travel from Florence into Chianti by minivan for two wine tastings, local meats, cheeses and olive oil, a winery visit, and free time in Radda. Guides such as Anna, Chiara and Katerina have led the outing, which suits anyone wanting Tuscan wine country without arranging a car.

“Wow, what an amazing tour through Chianti Classcio. Out tour guide Chiana was superb, being a local and providing insight to not only the wines, and history but also tips and recommendations. Not a bad way and great value to spend 6 hours with someone doing the driving in comfort. Highly recommend!”

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13.Chianti Wineries Tour with Tuscan Lunch and San Gimignano

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

Join a small group of up to 16 from Florence for two Chianti winery visits, wine tastings, a traditional Tuscan lunch, and free time in San Gimignano. Guides such as Daniel, Lorenzo, Christian, and Leonardo are praised for local insight, humor, and keeping the day relaxed.

“This was part of an end of life trip for me (stage 4 cancer) with my two adult daughters and my oldest daughter’s husband. We are traveling to Venice, Florence, Rome, Catania, Sorrento, Naples. I love wine and wineries and so this was probably the excursion I was most looking forward to. Tour guide was great. First winery—very dynamic host and good wine. 2nd winery-not as personal, great lunch, but not great wine. Trip to San Gimignan beautiful and fun but felt rushed. Driver said he would take my daughter back after last winery to the place that specializes in tiramisu but he did not. Overall good-but we enjoyed the…”

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14.Tuscany Day Trip: Chianti & Cooking Class Small Group

★★★★★★★★★★4.5 · 770 reviews · 11 hours 30 minutes (approx.) · from $167

Travel from Florence through Chianti and southern Tuscany by air-conditioned coach or minivan. Explore Castellina, Monteriggioni, San Gimignano, and Certaldo, then cook and eat a Tuscan lunch at Agricola Poggio Ai Laghi. Guides such as Marco, Marta, and Emma have earned praise, but the day is long and walking is hilly.

“The night before the trip, I started to feel sick, I called Viator to try to cancel this activity and get a refund. They kept repeating the 24 hour cancellation policy over and over again. They didn’t really care if a person with Covid goes to that activity and make 50 people sick. I did not get a refund and on top of that they offered to cancel the trip without a refund for us to be able probably to book others ! I had also booked another activity through Viator that I couldn’t go due to a storm and no ferry availability. Same thing repeating the 24 hour policy…”

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15.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. Expect quiet roads, a medieval village, winery visit, wine and olive oil tasting, and a Tuscan meal.

“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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