Chianti Wine Tours


FLORENCE · ITALY

15 Best Chianti Wine Tours In Florence

The best of Florence and Tuscany.

The 15 most popular chianti wine tours in Florence. The ones worth booking ahead for, with what each costs, how long it runs and who operates it.

15 Best Chianti Wine Tours In Florence

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - Siena with a guided city walk: Cathedral floor, contrade culture, and Piazza del Campo
1-Day Tours, Chianti Wine Tours, Florence, Lunch Experiences, Pisa & Leaning Tower Day Trips, Siena & San Gimignano Day Trips, Tour Reviews, Tuscany Day Trips, Wine Tours

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

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1.Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

A full-day coach tour from Florence covering Siena, San Gimignano, Pisa, and Chianti winery lunch with wine tasting options.

Most Popular★ 5.0

“The best of Tuscany tour was extremely enriching and an unforgettable experience. The entire trip conducted by Alex was exemplary and very well paced. Every single experience, from walking down the streets at Siena, to hearty lunch and wine tasting at Chianti, from walking down the old town of San Gimignano to witnessing the majestic…”

21,634 reviews11 to 12 hours (approx.)From $114.88by Walkabout Florence Tours

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Florence: Pisa, Siena, San Gimignano, and Chianti Experience - Starting at Santa Maria Novella: The Meeting Point That Matters
Chianti Wine Tours, Florence, Pisa & Leaning Tower Day Trips, Siena & San Gimignano Day Trips, Tour Reviews

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

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Florence: Chianti Wineries Tour with Wine Tasting - The drive into the Chianti Hills: where the day really starts
Chianti Wine Tours, Florence, Food & Drink, Tour Reviews, Tours, Wine Tours

Florence: Chianti Wineries Tour with Wine Tasting

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Small-Group Wine Tasting Experience in the Tuscan Countryside - Olive oil and local oil-and-wine harmony: what the pairing actually adds
Chianti Wine Tours, Florence, Food & Drink, Tour Reviews, Tuscany Day Trips, Wine Tours

Small-Group Wine Tasting Experience in the Tuscan Countryside

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4.Small-Group Wine Tasting Experience in the Tuscan Countryside

Small-group Chianti wine tasting from Florence with two winery visits, vineyard tours, olive oil tastings, and local cured meats.

★ 5.0

“We had an amazing Chianti wine tour with lovely hosts Jonathan and Francesco. From start to finish, the experience was excellent and felt truly personalised. We visited two great wineries with very knowledgeable producers who are passionate about their region. The wine selection was outstanding, with fantastic variety and quality. I would highly recommend this…”

7,392 reviews4 hours 45 minutes (approx.)From $107.63by Prestige Rent

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Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing - Starting in Florence: Piazzale Montelungo at 7:30 am
1-Day Tours, Chianti Wine Tours, Florence, Lunch Experiences, Pisa & Leaning Tower Day Trips, Siena & San Gimignano Day Trips, Tour Reviews, Wine Tours

Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

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5.Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

Florence day trip to Siena, San Gimignano, and Pisa with a Tuscan winery lunch and optional wine pairing, plus guided city highlights.

★ 4.5

“It was great! The description was exactly what the tour was. The timing of the day overall was good. The Siena tour guide was amazing. Good value for the money. Our group was a family of four-couple with kids aged 9 & 12. My kids loved it.”

6,006 reviews12 hours (approx.)From $78.60by Ciao Florence Tours Srl

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SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence - Val d’Orcia in One Day: Brunello and Montepulciano With a Pienza Cheese Farm Lunch
Chianti Wine Tours, Florence, Food & Drink, Tour Reviews, Tours, Tuscany Day Trips, Wine Tours

SMALL-GROUP Wine Safaris: Tuscan Wine Tasting Tours from Florence

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Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe - Cheese stop energy: Pecorino and Parmigiano, no theater
Chianti Wine Tours, Evening Experiences, Florence, Food, Food & Drink, Food & Wine Tours, Tour Reviews, Tours, Wine Tours

Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

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7.Winner 2025 Florence Sunset Food & Wine Tour by Eating Europe

Florence sunset food and wine tour with a Prosecco toast, 4 Tuscan wines, a Negroni lesson at wine windows, and artisan gelato.

★ 5.0

“Wonderful tour, great food and wine, a nice way to explore this interesting neighborhood across the Arno. Antonella was our guide — a funny, lively personality who made everyone laugh and have a really good time. Highly recommend her and the tour. A delightful way to spend an evening!”

5,015 reviews3 hours 30 minutes (approx.)From $149.95by Florence Food Tours by Eating Europe

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery - Siena’s Duomo and Piazza del Campo: where the medieval vibe clicks
Chianti Wine Tours, Florence, Lunch Experiences, Pisa & Leaning Tower Day Trips, Siena & San Gimignano Day Trips, Tour Reviews, Wine Tours

From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

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8.From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

A full-day Tuscany trip from Florence with guided Siena, free time in San Gimignano, Pisa highlights, and optional Chianti lunch and wine tasting.

★ 4.8

“What a day! Thank you Manolo for a wonderful day full of laughs and learning about the history of the Tuscany region. This was a great way to see so much of the beautiful Tuscan landscape and hospitality, topped off with a climb up the Leaning Tower of Pisa at sunset. Such great value for…”

4,538 reviews12 hoursFrom $112by Walkabout Tours

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - San Gimignano: UNESCO Towers, Frescoes, and the Most Manageable First Stop
1-Day Tours, Chianti Wine Tours, Florence, Food & Drink, Lunch Experiences, Siena & San Gimignano Day Trips, Tour Reviews, Wine Tours

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

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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch - Pisa’s Square of Miracles: what you can do with 80 minutes
Chianti Wine Tours, Florence, Lunch Experiences, Pisa & Leaning Tower Day Trips, Siena & San Gimignano Day Trips, Tour Reviews, Wine Tours

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

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Chianti Wine Tour from Florence - Stop Two: Vineyard Slope Walk, Cellars, Aromatic Garden, and Multiple Tastings
Chianti Wine Tours, Florence, Tour Reviews, Tours, Wine Tours

Chianti Wine Tour from Florence

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11.Chianti Wine Tour from Florence

Coach tour from Florence to two Chianti wineries on the Via Chiantigiana. Tastings, local foods, and views on English tours.

★ 4.5

“Very nice wines and a small bit of food. 3 wines in each place, mainly red wine which is what the area is known for. Guides were very nice and knowledgable, would recommend”

3,979 reviews5 hours (approx.)From $59.13by CAF Tour and Travel

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From Florence: Small Group Wine Tasting Tour to Tuscany - The two-estate format: why it beats the “one winery” tasting
Chianti Wine Tours, Florence, Food & Drink, Tour Reviews, Tours, Tuscany Day Trips, Wine Tours

From Florence: Small Group Wine Tasting Tour to Tuscany

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12.From Florence: Small Group Wine Tasting Tour to Tuscany

Small-group Chianti Classico wine and olive-oil tastings from Florence. Visit two estates, sample six wines, enjoy local pairings.

★ 4.9

“I went on this tour with my husband. We had so much fun! Jason was an amazing guide. He was hilarious and so friendly. The two wineries we went to had wonderful tastings as well as delicious snacks. The wineries had beautiful views to take photos of (which Jason also helped with). The ride there…”

3,902 reviews4.5 hoursFrom $105by Prestige Rent - Tours in Italy

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Siena, San Gimignano and Chianti Wines Day Tour from Florence - Monteriggioni: Quick Fortress Time With Optional Wall Views
Chianti Wine Tours, Florence, Siena & San Gimignano Day Trips, Tour Reviews, Tours, Wine Tours

Siena, San Gimignano and Chianti Wines Day Tour from Florence

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

Full-day Tuscany trip from Florence: UNESCO Siena and San Gimignano, medieval Monteriggioni, plus Chianti tastings and snacks. From $78.60.

★ 4.5

“It was a good tour bit of a big tour but a very good tour.. You can miss the optional lunch which wasn't good at all and there are far better places to eat in Sienna. Also do take the optional Sienna tour which was very good.”

2,542 reviews10 hours 30 minutes (approx.)From $78.60by Ciao Florence Tours Srl

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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch - Meeting at Piazzale Montelungo and managing the 11-hour clock
Chianti Wine Tours, Florence, Food & Drink, Lunch Experiences, Siena & San Gimignano Day Trips, Tour Reviews, Wine Tours

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

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From Florence: Chianti Half-Day Afternoon Tour - The 6-hour rhythm: bus rides, photo stops, and why timing matters
Chianti Wine Tours, Florence, Half-Day, Tour Reviews, Tours

From Florence: Chianti Half-Day Afternoon Tour

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15.From Florence: Chianti Half-Day Afternoon Tour

Chianti wine country from Florence: cellar tours, 7 wine tastings, olive oil and balsamic samples, plus free time in Monteriggioni.

★ 4.4

“Valesca (tour guide) and Viaggio (the driver) were amazing!! Very informative and attentive with everybody, there was a group of roudy teens in the tour and the guide handled it very well accommodating the rest and making sure we all enjoyed . The wine variety was wide and the information was clear in every stop,…”

2,328 reviewsFrom $55.80by My Tour in Italy

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