Florence · CHIANTI WINE TOURS

Chianti Wine Tours from Florence: 15 Days Among the Sangiovese Vines

53 tours  ·  from $41 a head

The Chianti is a region of small estates on winding roads, which is why almost everybody goes with a driver. The 15 below compare the half days, the full days with lunch, and the ones that fold in Siena or San Gimignano.

Florence: Pisa, Siena, San Gimignano, and Chianti Experience - Pisa: a short visit for the famous tower
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Florence: Pisa, Siena, San Gimignano, and Chianti Experience

1.Pisa, Siena, San Gimignano, and Chianti Experience

★★★★★★★★★★4.5 · 8,393 reviews · 12 hours · from $52Our pick

Travel from Florence by Wi-Fi-equipped bus to Pisa, a Chianti winery, San Gimignano and Siena. Choose a light lunch and wine tasting, a guided walk in Siena, and Leaning Tower tickets. Guides such as Barbara, Anna and Layla share local context and practical tips, while the long drive between stops offers time to rest.

“Emma our your guide went above and beyond. Our experience was great and so worth it! We took my grandpa who is 80 years old and he loved it! We saw so much stuff in just one day!”

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Florence: Chianti Wineries Tour with Wine Tasting - Between stops: a short ride and another view of the region
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Florence: Chianti Wineries Tour with Wine Tasting

2.Chianti Wineries Tour with Wine Tasting

★★★★★★★★★★4.5 · 8,301 reviews · from $56

Ride from Florence to two Chianti wineries for vineyard walks, winemaking introductions, and tastings of up to seven wines in all. Your English-speaking tour leader shares local context en route; winery hosts explain their wines and serve Tuscan snacks. Expect about 5.5 hours away, with coach transport and no lunch included.

“Such an incredible time! Cecilia was our guide and did a wonderful job. The host at the first winery was also incredibly knowledgeable and exciting when telling us about the wine and history. Highly recommend!”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - San Gimignano: towers, lanes, and a short window
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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

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

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

Leave Florence by coach for San Gimignano, Monteriggioni (April to October), a Chianti winery lunch and tasting, and Siena. Expect free time in the towns, with a Siena walking tour and cathedral entry available only on selected options. Guide teams vary; past departures have included Sandro, Ricardo, Marta and Ilaria.

“Other reviews are correct- this is not a guided tour. However, I liked how we are on our own in each city rather than having to keep up with a guide and large group. Hilary was very sweet and gave us information about each city before exiting the bus. The winery was just a tasting experience (4 wines) with lunch. I thought they gave us a lot of food: bruschetta, meats, cheese, a full portion of pasta with ragu, and biscotti. Personally I was full after it. The employees there were very energetic and fun. Be prepared for a lot of walking. Uneven streets and hills. This tour is not…”

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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch - Pisa: the Field of Miracles in 80 minutes
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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

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

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

Travel by air-conditioned coach from Florence to Pisa, San Gimignano and Siena, with a scenic drive through Chianti. You get free time in each town, plus an optional lunch with three wines and Vin Santo. A Siena guide and cathedral entry are included only with selected options.

“Love our guide, Santo! And Paul at Siena! Very professional and informative.”

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Chianti Wine Tour from Florence - The second estate brings vineyard and cellar together
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Chianti Wine Tour from Florence

5.Chianti Wine Tour from Florence

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

Leave the driving to a licensed tour leader on this five-hour coach trip from Florence into Chianti. Visit two organic wineries for wine, local food, vineyard and cellar tours, with a scenic ride along the Via Chiantigiana. English and Spanish tours are available. Expect some walking on slopes, and note that tasting food is not a full meal.

“Great trip, lovely guide. Super vineyards and views. Maybe an age limit would be a good idea. A small child was obviously unimpressed with the whole experience.”

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From Florence: San Gimignano, Siena, and Chianti Wine Tour - Siena: a quick look at a remarkable city
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From Florence: San Gimignano, Siena, and Chianti Wine Tour

6.San Gimignano, Siena, and Chianti Wine Tour

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

Leave Florence by air-conditioned bus or minivan for Siena, a Chianti estate, and San Gimignano. You get free time in both towns, a guided winery visit, five wine tastings, and a Tuscan meal featuring truffle lasagna, cheeses, cured meats, and more. Guides have included Marco, Lyla, and Marta, though assignments vary.

“Great experience, Lyla was a great guide. Very well coordinated and overall very fun!”

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Siena, San Gimignano and Chianti Wines Day Tour from Florence - Monteriggioni: a compact first taste of medieval Tuscany
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Siena, San Gimignano and Chianti Wines Day Tour from Florence

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

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

Ride from Florence through central Tuscany to hilltop Monteriggioni, Siena and San Gimignano. The Classic option adds a guided Siena walk; the Semi-Independent option gives you more time to explore alone. Finish with a tasting of up to three Chianti wines and regional snacks. Expect a long day, shared coach and plenty of walking.

“Nice Tuscany day tour. Alex was great in explaining about the various areas we visited, and the driver Cozimo did a good job getting us back safe.”

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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch - Lunch and wine in the Chianti hills
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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

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

★★★★★★★★★★4.6 · 2,427 reviews · from $89

Travel by air-conditioned bus from Florence to San Gimignano, Siena and the Chianti hills, with a multilingual escort and free time in the towns. A winery stop pairs a Tuscan-style lunch with a guided tasting of three wines. Add a local Siena guide and Cathedral entry if you want a closer look at the city’s landmarks.

“Hilary led us through a well organised and informative tour of Tuscany. The towns were beautiful and the lunch experience excellent.”

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From Florence: Chianti Half-Day Afternoon Tour - Getting to Villa Costanza without a taxi bill
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From Florence: Chianti Half-Day Afternoon Tour

9.Chianti Half-Day Afternoon Tour

★★★★★★★★★★4.4 · 2,328 reviews · from $55

Ride from Florence to two Chianti wine estates for cellar visits and seven wine pours, plus olive oil, balsamic vinegar, bread and salami. You’ll also have time to walk around medieval Monteriggioni. Guides such as Marta, Andrea and Marco have led the tour, though the guide may vary. Meet at Villa Costanza, reached by tram from central Florence.

“Very nice experience. Everything was perfect. The vineyards very interesting and Toscana very beautiful.”

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Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - A winery lunch that breaks up the bus-and-monument rhythm
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Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti

10.Day Trip to Pisa, Siena, San Gimignano, and Chianti

★★★★★★★★★★5.0 · 2,283 reviews · 12 hours (approx.) · from $78Top rated

Leave Florence at 7:30 am by air-conditioned coach for a full day among Tuscany’s best-known towns. Expect a guided walk in Siena, free time in San Gimignano and Pisa, and, on qualifying options, a winery lunch with four wine tastings. The Leaning Tower is a photo stop, not an included climb.

“I definitely recommend this trip! Sienna and Gimignano were amazing. Pisa was more of just a picture opportunity, but happy we got to see it as well.”

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Half day Chianti Vineyard Escape from Florence with Wine Tastings - Choosing a morning or afternoon departure
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Half day Chianti Vineyard Escape from Florence with Wine Tastings

11.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 wine estates with an English-speaking tour leader. Expect cellar and vineyard visits, up to four wine samples at each stop, olive oil and regional food tastings, and a photo stop in the countryside. Guides have included Alex, Lorenza, Cecilia, Anna, and Ezgi, though your guide may differ.

“Everything about this excursion was great! Fantastic communication leading up to it. Both wineries were awesome in their own way. The first was more of a small family business while the second seemed a little "classier." Great views at both. Comfy ride. If you're looking for an escape from the city, I highly recommend!”

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Chianti Vespa Tour with Lunch from Florence & E-car Option - A practice loop before the road ride
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Chianti Vespa Tour with Lunch from Florence & E-car Option

12.Chianti Vespa Tour with Lunch from Florence & E-car Option

★★★★★★★★★★5.0 · 1,453 reviews · 6 hours 30 minutes (approx.) · from $125

Leave central Florence by minivan, learn the basics, then follow a guide through Chianti’s vineyard roads on a Vespa or in a Fiat Topolino e-car. The roughly six-and-a-half-hour outing includes scenic stops, a winery visit, a Tuscan lunch, and wine and olive oil tastings. You need a valid driving license to drive a Vespa; a passenger or e-car can be a better fit if you do not ride scooters.

“The Vespa tour through the countryside was amazing. Not much traffic on the roads and the guides were very good at keeping it safe. Alex and Alah were fun and energetic. The winery with the Tuscan lunch was excellent, the wines were excellent also. My wife was skeptical of riding on the Vespa at first, but within minutes was loving it. Highly recommend.”

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Tuscany Bike Tours Through the Chianti Hills with Wine Tasting - Taking in the views without rushing
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Tuscany Bike Tours Through the Chianti Hills with Wine Tasting

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

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

Leave Florence by van for a roughly two-hour ride through Chianti vineyards, olive groves and country lanes, guided by a local cycling lead such as Angus, Ben or Alessio. Stop for views, then visit a castle winery for wine and olive oil tastings and lunch. A support van can help you skip the steep hill; e-bikes cost extra.

“I highly recommend this tour especially if you want to get out of Florence and explore the countryside without going too far away. I am a solo traveler and I felt comfortable. If you’re like me and need to know all the details before you do something, here is the breakdown: You meet your guide at their storefront. Use the bathroom at a nearby cafe before leaving! Then you walk to a parking lot and get in a sprinter van and drive to the castle. The ride isn’t too long but it’s beautiful. It’s a very windy road! At the castle you’re given a bike, helmet, water, and some safety…”

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Essence of Chianti Small Group Tour with Lunch and Tastings from Florence - Riseccoli begins with hills, vines and olive oil
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Essence of Chianti Small Group Tour with Lunch and Tastings from Florence

14.Essence of Chianti Small Group Tour with Lunch and Tastings from Florence

★★★★★★★★★★5.0 · 1,269 reviews · 8 hours (approx.) · from $180

Leave Florence at 9 a.m. for an eight-hour Chianti day: visit three wineries, taste local wines and olive oil, eat a Tuscan lunch, and spend time in Greve. Guides such as Jason, Valentina and Leo have led past tours, but assignments vary. The group can reach 25, and the winery stops may change.

“Beautiful sites and delicious wine! Our guide, Davide, was so informative, kind, and fun. This experience is one that we will never forget and we are so glad that we booked it.”

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From Florence: Chianti Wine Tour with Tastings - The second winery: vines, cellar and garden
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From Florence: Chianti Wine Tour with Tastings

15.Chianti Wine Tour with Tastings

★★★★★★★★★★4.4 · 1,025 reviews · from $62

Leave Florence by air-conditioned bus for two organic wineries in the Chianti Classico region. You’ll taste three to four wines at each stop, try local products such as pecorino, and hear about winemaking from winery hosts and an English- or Spanish-speaking guide. Expect about five hours out, including scenic drives and some uphill and downhill walking.

“This tour was awesome, our guide Alessia (Alexa) was perfect and we had a fantastic experience at both wineries where the staff were friendly, funny and educated us about the different wines! Highly recommend!! We also met some great travelers in our group!”

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New in Chianti Wine Tours

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