Wine Tours

TUSCANY

10 Best Wine Tours In Siena

Most booked first.

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

10 Best Wine 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.

“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.”

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.

“This tour was a wonderful experience! We visited three distinct wineries and tasted a variety of Rosso and Brunellos. We had a great lunch that was homemade in the family kitchen. The drive was beautiful and Emanuel, our “professional drive” (as he calls himself), is fantastic! He made our day showing us the sights and…”

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

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From Siena: Chianti and Castles Tour with Wine Tastings

From Siena: Chianti and Castles Tour with Wine Tastings - Castellina in Chianti: Walled-Town Energy Without the Full Hike

3.From Siena: Chianti and Castles Tour with Wine Tastings

★ 4.6

5-hour Chianti tour from Siena with a small minivan, Castellina and Monteriggioni, plus two winery tastings with snacks and views.

“A wonderful small group tour visiting the beautiful Chianti region & several wineries snd hill top Tuscan villages. Momo our tour guide was an excellent host- very informative, friendly and helpful. Enjoyed some beautiful Chianti wines. It was a most enjoyable and relaxing five hours! Excellent value.”

631 reviews5 hoursFrom $100by My Luxury Drive

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Total Immersion Wine Tour in Chianti

Total Immersion Wine Tour in Chianti - Rooftop Introduction: Black Rooster Story and Chianti Views at 600 Meters

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

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

★ 4.9

Small-group Brunello day trip from Siena to Montalcino: 3 winery tastings, a family lunch, medieval town time, and Sant’Antimo Abbey.

“Our day touring the wineries with Manu was excellent. The tour was wonderful, and the people we met at the wineries were friendly informative and of course the wine was sublime. Most of all our guide made the day lots of fun, he gave lots of interesting infformation and history and was completely charming. 100%…”

357 reviewsFrom $203.91by Tuscan Escapes by Papilio

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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)

6.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.

“It was informative, & most enjoyable. Our host was very passionate, about organically growing the grapes & the olive trees. The lunch was very delicious.”

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

7.From Siena: Tuscany Hills Wine Tour

★ 4.1

Full-day Chianti and Val d’Orcia wine tour from Siena with two tastings, olive oil, and stops in Pienza and Montepulciano.

“The trip through the countryside was beautiful. At the Chianti tasting the presenter was so difficult to understand with her strong accent. .Definitely enjoyed the wine more at the second place. Disappointed that there was no olive oil tasting as well. Overall it was a very enjoyable day with a fun group.”

323 reviewsFrom $146.14by My Tour in Italy

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Siena: Pasta and Tiramisu Cooking Class with Wine

Siena: Pasta and Tiramisu Cooking Class with Wine - The 3-Hour Pasta Workshop: Eggs Pasta, Pici, and Potato Gnocchi

Wine Class – Tuscan Classics

Wine Class - Tuscan Classics - How the class actually teaches you to taste (swirl, smell, sip, repeat)

9.Wine Class – Tuscan Classics

★ 5.0

Two hours in central Siena to learn Tuscan wine basics through a guided tasting of 6 wines plus local bites in English.

“The class was phenomenal! The instructor was very passionate about teaching the class ! Very knowledgeable, very sincere.”

264 reviews2 hours (approx.)From $72.59by Papilio srl

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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

10.A Brunello Cooking Class with Vineyards View Winery

★ 5.0

Hands-on pasta in Montalcino with vineyard views. Tour a 13th-century castle winery, then enjoy a Brunello-paired lunch.

“Wonderful is how I would describe this. Chef Alexandra was so engaging and made this experience exceptional. We enjoyed the classic farmhouse setting and the small group (eight) class. We definitely learned the basics and some great tips for making pasta, and had a wonderful time relaxing on the terrace enjoying our food, with wine,…”

221 reviews4 hours (approx.)From $313.35by Forzoni Tours

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