Florence · CHIANTI WINE TOURS

The 15 Best Chianti Wine Tours from Florence

205 tours  ·  from $25 a head

The Chiantigiana runs south through Greve and Panzano and every second gate is a cellar. These 15 sort the half-days that get you back for dinner from the full days with lunch and a hill town, priced, timed and clear about how many estates you actually visit.

Florence: Pisa, Siena, San Gimignano, and Chianti Experience - Meeting at Santa Maria Novella
Chianti Wine Tours, Pisa Day Trips, San Gimignano Day Trips, Siena Day Trips, Tour Reviews

Florence: Pisa, Siena, San Gimignano, and Chianti Experience

Florence: Chianti Wineries Tour with Wine Tasting - First winery: learning the basics with a Tuscan tasting
Chianti Wine Tours, Tour Reviews, Tours, Wine Tours

Florence: Chianti Wineries Tour with Wine Tasting

2.Chianti Wineries Tour with Wine Tasting

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

Escape Florence for two Chianti wineries, Tuscan wines, local snacks, rolling hill views, and a practical half-day outing for $56.37.

“Tour was amazing. The transportation was easy and accessible to find. The guide was informative throughout the whole ride there. Our favorite part were the two wineries. We loved our experience and would want to book again!”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - San Gimignano: towers, alleys, and a tight timetable
Chianti Wine Tours, Day Trips from Florence, Lunch Experiences, San Gimignano Day Trips, Siena Day Trips, Tour Reviews, Wine Tours

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

Explore San Gimignano, Siena, Monteriggioni, and Chianti from Florence with a winery lunch, three wines, and free time.

“Guide Alejandra was knowledgeable and give us the information in English and Spanish. The three medieval towns were charming and worth visiting as well as the family owned winery and olive oil producers. The Tuscan meal was simple (typical) and good. The family vineyard owners were charming and friendly so we had a lovely time. Their gift shop was good and we were lucky to have just been able to buy the new production of extra virgin olive oils for 2025 which were available just this week!!! Their dessert wine was delicious so we bought a bottle. All in all it was a fun experience. We did have an issue…”

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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch - Meeting at Piazzale Montelungo
Chianti Wine Tours, Lunch Experiences, Pisa Day Trips, Siena Day Trips, Tour Reviews, Wine Tours

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

See Pisa, San Gimignano, Chianti, and Siena in one long Tuscan day, with bus transport, optional lunch, wine tasting, and a Siena guide.

“Our tour guide Marta was perfect. She explains everything with details and we really enjoy the experience. The day trip is worth it. Also, really thanks to Silvio, the driver! 🤍”

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Chianti Wine Tour from Florence - First winery: organic production and a personal welcome
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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

Review of the 5-hour Chianti wine tour from Florence, with two organic wineries, Tuscan tastings, scenic views, costs, and practical tips.

“Great experience in Toscana, the tour guide Alessandra was great, we visited two vineyards, test wines and food, and the beautiful landscape of Chianti. Our deiver Massimo was great”

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From Florence: San Gimignano, Siena, and Chianti Wine Tour - Siena and the space around Piazza del Campo
Chianti Wine Tours, San Gimignano Day Trips, Siena Day Trips, Tour Reviews, Tours, Wine Tours

From Florence: San Gimignano, Siena, and Chianti Wine Tour

6.San Gimignano, Siena, and Chianti Wine Tour

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

See Siena, Chianti, and San Gimignano in one full day from Florence, with five wine tastings, a Tuscan lunch, and free time in medieval towns.

“We had an incredible adventure through Chianti and surrounding towns. Marco was an excellent guide who is very knowledgeable of Tuscan and Italian history. San Gimingnano was the highlight filled with delicious treats and sights of the picturesque rolling hills.”

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Siena, San Gimignano and Chianti Wines Day Tour from Florence - Meeting the coach near Santa Maria Novella
Chianti Wine Tours, San Gimignano Day Trips, Siena Day Trips, Tour Reviews, Tours, Wine Tours

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

Review of a full-day Tuscany tour from Florence to Siena, San Gimignano, Monteriggioni, and a Chianti wine estate.

“Beautiful countryside and interesting places to see. The reason rating not higher was it combined 3 languages on same tour Made it complicated. Winery was a commercial operation. Hoped the wine tasting to be overlooking the Tuscan hills”

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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch - Meeting at Piazzale Montelungo
Chianti Wine Tours, Lunch Experiences, Siena Day Trips, Tour Reviews, Wine Tours

Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

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

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

Review of Florence’s Tuscany day trip to San Gimignano, Siena, Monteriggioni, and a Chianti winery lunch with three wine tastings.

“Fantastic Day Trip! We had a wonderful experience on this tour. Guides, Marta and Stella, were incredibly friendly, knowledgeable, and organised. They made sure everyone was comfortable and informed throughout the day. Our driver, Elis, was professional and smooth—navigating the scenic Tuscan roads with ease. This tour is a great value for the price and perfect for travelers looking for a stress-free way to visit iconic locations in Tuscany. Highly recommend!”

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Tuscany: Day Trip to Pisa, Siena, San Gimignano, and Chianti - Reaching Pisa and the Field of Miracles
Chianti Wine Tours, Day Trips from Florence, Pisa Day Trips, San Gimignano Day Trips, Siena Day Trips, Tour Reviews, Tuscany Day Trips

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

See Pisa, Siena, San Gimignano, and Chianti in one long, food-filled day from Florence, with a Siena guide, cathedral visit, lunch, and wine tasting.

“Our tour guide , Fabiana, was absolutely amazing. I travel with two elderly parents and she was more than accomodating and helped us stay with the group. The views and different tours were amazing and fun.”

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Half day Chianti Vineyard Escape from Florence with Wine Tastings - First estate: wine, local food, and a closer look at production
Chianti Wine Tours, Tour Reviews, Wine Tours

Half day Chianti Vineyard Escape from Florence with Wine Tastings

Chianti Vespa Tour with Lunch from Florence & E-car Option - Learning to ride before the country roads
Chianti Wine Tours, Lunch Experiences, Motorbike & Scooter Rentals, Scooter Rentals, Tour Reviews, Tours, Vespa Tours

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

Ride a Vespa through Chianti from Florence, stopping for Tuscan views, winery visits, wine, olive oil, and a traditional lunch.

“We had such a great time even though I was not able to ride the Vespa, the guides were so patiently trying to teach me and I just couldn’t figure it out. Riding double was great also. Great information and sites. The lunch was amazing, a capris salad and risotto. The wine tasting was so good we left with a bottle of great wine. Thank you for a wonderful experience.”

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Tuscany Bike Tours Through the Chianti Hills with Wine Tasting - Pedaling past vineyards, villas, and olive groves
Chianti Wine Tours, Florence Bike Tours, Tour Reviews, Tours, Tuscany Day Trips, Wine Tours

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

Cycle through Chianti from Florence, stop at a medieval castle for wine, olive oil, and lunch, with guides, transport, and support included.

“We had really a fun time. Right from the start the happy enthusiastic vibe from the staff set the vibe for the day. Angus was our guide on the bike and had lots of interesting information and kept us safe. Really appreciated that he was able to take photos for us as my phone died at the beginning. The ride has lots of scenic views across the rolling countryside and is 90% either flat or downhill. There is a “challenging” short hill that some may prefer to take the sag wagon on offer but the gearing on the bikes are very suited to the steepness. In general the bike worked…”

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Essence of Chianti Small Group Tour with Lunch and Tastings from Florence - Greve in Chianti: 45 minutes in the region’s main village
Chianti Wine Tours, Lunch Experiences, Tour Reviews, Tours

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

Spend a full day in Chianti with three winery visits, Tuscan lunch, generous tastings, Greve village, and scenic transport from Florence.

“The wine tour for each winery was different- some explained a lot, some did not. The food at our second winery was good. The last one we reused our wine glass 3 times for each tasting and did not have a good food pairing. Daniele and Irene were fantastic! We started around 9am and were done by 5pm.”

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From Florence: Chianti Wine Tour with Tastings - First winery: small-scale Chianti with a personal welcome
Chianti Wine Tours, Tour Reviews, Tours, Wine Tours

From Florence: Chianti Wine Tour with Tastings

15.Chianti Wine Tour with Tastings

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

Spend five hours touring two Chianti wineries from Florence, with cellar visits, Tuscan food, scenic hills, and generous wine tastings.

“Excellent tour, very professional and knowledgeable guide and 2 great wineries visited. Great value for the price and length.”

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