Tuscan Winery Tours

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10 Best Tuscan Winery Tours In Siena

Most booked first.

Our shortlist of the 10 most-booked tuscan winery tours around Siena, ranked by what travellers actually rated. Who runs them, how long they take, what they cost.

10 Best Tuscan Winery Tours In 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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Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena - Stop 1: Tuscan vineyards, cellars, and your first Brunello tasting

2.Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

★ 5.0

Small-group Brunello trip from Siena with 3 winery tastings, free time in Montalcino, Sant’Antimo abbey, and a hearty included lunch.

“Giorgia was an excellent guide to the best wine we experienced in Italy! She was full of interesting facts and history of the region. It made the experience lively and educational. She made sure all in the tour were included in conversation and all of us had a great time! Our favorite winery was Fattoria…”

952 reviews9 hours (approx.)From $217.67by Tuscan Escapes by Papilio SRL

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From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch

From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch - Montalcino Hill Town Time: Fortress Views and Easy Browsing

Siena: A Wine Tour and Tasting Experience

Siena: A Wine Tour and Tasting Experience - Stop 2 in the Cellar: From Crushing to Bottling (and Why It Matters)

5.Siena: A Wine Tour and Tasting Experience

★ 5.0

Organic vineyard and cellar tour outside Siena with four wine tastings, olive oil, and a light lunch in a small English group.

“This was a great tour that showcased wines and olive oils of the region. A lot of wineries focus on their own history and processes, but this one went into a lot of general wine principles, including proper tasting methods, pairing, etc. The light lunch was very delicious as well. Highly recommend this tour.”

352 reviews3 hours (approx.)From $102.84by Az. Agr. La Lastra

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From Siena: Tuscany Hills Wine Tour

From Siena: Tuscany Hills Wine Tour - The Monteriggioni start and the Chianti winery tasting you’ll remember

A Brunello Cooking Class with Vineyards View Winery

A Brunello Cooking Class with Vineyards View Winery - Getting there from Siena or Florence without turning the day into a hassle

San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting - Florence to the First Stop: A Day That Starts Early

9.San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

★ 4.5

A full-day escorted tour from Florence featuring San Gimignano, Monteriggioni, Siena, and a Chianti winery lunch with wine tasting.

“Martha was the host, she was great! She always had lots of info for each place we visited. Such nice towns we visited. Love the area! Would recommend the tour.”

171 reviews11 hours (approx.)From $95.58by CAF Tour and Travel

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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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