Chianti Wine Tours

TUSCANY · DESTINATION

10 Best Chianti Wine Tours From Siena

Most booked first.

Our shortlist of the 10 highest-rated ways to spend a day in the Chianti hills. Castle estates, family-run vineyards, lunch under the cypress — the wine roads that start half an hour out of Siena.

10 Best Chianti Wine Tours From Siena

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

From Florence: San Gimignano, Siena, and Chianti Wine Tour - Starting point in Florence: meet near the Baptistery

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

Most Popular★ 4.5

Florence to Siena, San Gimignano, and Chianti in one full day with guided history, five wine tastings, and a Tuscan lunch.

“The experience couldn’t get any better. Marco is an excellent guide and a person! Highly recommended. I went by myself, but made very good friends along the way 💫 Italy is mesmerizing and do not hesitate to take this tour 🥰🌟 p.s. I would recommend to get lunch at the winery. Grazie”

3,762 reviewsFrom $164.26by My Tour in Italy

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Siena: San Gimignano, Chianti & Montalcino Small-Group Tour

Siena: San Gimignano, Chianti & Montalcino Small-Group Tour - A small-group van with a bilingual escort (and why that helps)

Hidden Castles & Chianti Wine Experience– Small Group

Hidden Castles & Chianti Wine Experience– Small Group - Where You Meet in Siena (and Why It Matters)

6.Hidden Castles & Chianti Wine Experience– Small Group

★ 4.5

Small-group Chianti wine tour from Siena with two tastings, 7 wines, olive oil and snacks, plus Castellina and Monteriggioni.

“Our guide Luca was very knowledgeable and gave great information all day throughout the tour. He had good recommendations for restaurants in the cities we visited, and explained the different wines and products very well. The tour itself was nice, with visits to two wineries and some cities with impressive views over the hillside in…”

172 reviews5 hours (approx.)From $59.13by myTour in Italy

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Siena: Small group Cooking Class in Chianti Farmhouse

Siena: Small Group Cooking Class in Chianti Farmhouse - The Tuscan Menu Focus: Pasta Skills Plus Starters and Tiramisu

San Gimignano, Chianti, and Montalcino Day Trip from Siena

San Gimignano, Chianti, and Montalcino Day Trip from Siena - Price and time: 11 hours, and why the early start matters

8.San Gimignano, Chianti, and Montalcino Day Trip from Siena

★ 4.5

An 11-hour Siena day trip hitting San Gimignano, Chianti wine country, and Montalcino for Brunello tastings plus classic Tuscan stops.

“Buyer Beware. This tour was a 3rd party vendor My tour 366, who rescheduled the tour and overbooked what was supposed to be an 8-12 semi-private tour to 28 people. The two wineries were not able to accommodate. we ended up in the production area at the last minute, not the tasting room. The bus…”

150 reviews11 hours (approx.)From $168.96by myTour in Italy

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Siena: Small Group Cooking Class in Chianti Farmhouse

Siena: Small Group Cooking Class in Chianti Farmhouse - The Tuscan Menu Focus: Pasta Skills Plus Starters and Tiramisu

9.Siena: Small Group Cooking Class in Chianti Farmhouse

★ 4.9

Cook classic Tuscan dishes at a Chianti farmhouse with Chef Simone. Small group lesson, wine, and a meal you make in 4 hours.

“Amazing!! Would highly recommend. We only had one other couple completing the class with us which was a nice quiet cooking experience. We had wine which was a treat! Our chef was very clear in his instructions and taught us how to make ravioli and tiramisu which we will try make at home! We really…”

146 reviewsFrom $130.28by My Tour in Italy

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Vespa Tour with Lunch&Chianti Winery from Siena

Vespa Tour with Lunch&Chianti Winery from Siena - Meeting point and “where do I actually start?”

10.Vespa Tour with Lunch&Chianti Winery from Siena

★ 4.0

Vespa through Chianti from Siena with wine tasting, vineyard cellars, and quick hill towns. Driver or passenger options.

“The tour itself was great. However, a Fiat 500 in our group was having mechanical issues, and we spent a large part of the tour waiting on the road for the car to be exchanged. This led to us missing all of our stops except the one at the vineyard. The vineyard was great, anRead…”

126 reviewsFrom $168.36by myTour in Italy

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