The 11 Best Siena Wine Tours

1.San Gimignano, Siena, and Chianti Wine Tour

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

Review of a full-day Tuscany tour from Florence to Siena, Chianti, and San Gimignano, with wine, lunch, free time, and practical tips.

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

★★★★★★★★★★5.0 · 952 reviews · 9 hours (approx.) · from $217Top rated

Taste Brunello at three family wineries, enjoy a homemade Tuscan lunch, and visit Montalcino and Sant’Antimo from Siena.

“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 offering lots of history about the area. Don’t miss this tour!”

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3.Chianti and Castles Tour with Wine Tastings

★★★★★★★★★★4.6 · 631 reviews · 5 hours · from $100

See Chianti from Siena in five hours with two wineries, Castellina, Monteriggioni, scenic drives, and generous Tuscan wine tastings.

“Fabulous tour with great local insights into culture, wine and food. Highly recommended”

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4.Total Immersion Wine Tour in Chianti

★★★★★★★★★★4.9 · 430 reviews · 2 hours · from $47Best value

Review of Fattoria di Montemaggio’s Chianti wine tour, with organic winemaking, six tastings, Tuscan views, food, access tips, and value advice.

“The tour was perfect! Only a group of 4 and the whole experience was amazing. We learned so much about wine making and Chianti. The wines we tried were really good. Worth all the money, totally reccomended!”

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5.A Wine Tour and Tasting Experience

★★★★★★★★★★5.0 · 352 reviews · 3 hours (approx.) · from $102

Review of La Lastra’s Siena wine tour: organic vineyards, four wines, Tuscan lunch, expert guidance, pricing, timing, and practical tips.

“Great value - generous pours and lovely large lunch! We enjoyed being in the vineyards as well as the fermentation room”

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6.A Brunello Cooking Class with Vineyards View Winery

★★★★★★★★★★5.0 · 221 reviews · 4 hours (approx.) · from $313

Review of a Brunello cooking class near Montalcino, with handmade pasta, castle and cellar tour, wine pairings, and terrace views.

“This was one of our favorite experiences in Italy! All of our children (ages 10-19) LOVED it! The food was delicious, the scenery beautiful and the wine magnificent! Don’t miss this experience…well worth it!”

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

★★★★★★★★★★4.5 · 171 reviews · 11 hours (approx.) · from $95

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

“Overall: Great destinations, great guide, poor lunch, too many people. Great tour guide, very friendly. Fantastic locations. Too many people for it to be personal at all. It’s a full double-decker Coach bus completely filled with people. If you get stuck sitting in the back of the bus, you have to wait for everyone else to get off first which wastes time at each location. Felt like a hierarchy of seating arrangement. Winery lunch was mediocre. Winery was not spectacular. They turn over hundreds of people a day and the food was basic. Lots of yelling to explain each wine.”

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8.Vespa Tour with Lunch&Chianti Winery from Siena

★★★★★★★★★★4.0 · 126 reviews · from $168

Review of Siena’s Vespa ride through Chianti, with village stops, winery tasting, lunch, safety advice, costs, and booking tips.

“We had a very fun and knowledgeable tour guide who made the trip such a great time! It was such a beautiful ride and the wine was amazing! We would definitely do it again!”

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9.Tuscany Hiking Tour from Siena Including Wine Tasting

★★★★★★★★★★5.0 · 112 reviews · 4 hours (approx.) · from $72

Hike the Via Francigena from Siena through Tuscan hills, then taste local wines and explore medieval Monteriggioni.

“This hike was long and a little strenuous at times, but we'll worth it. Our guide, Alessia was super nice and explained so much along the way. The final stop at Monteriggioni was great and we had plenty of time to explore on our own.”

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10.Organic Winery Tour and Wine Tasting

★★★★★★★★★★5.0 · 111 reviews · 2.5 hours · from $88

Tour Siena’s organic vineyards, learn Tuscan winemaking, taste five wines, and enjoy seasonal food at La Lastra for $88.

“We absolutely loved our experience. Gianluigi was very well informed, explicative and such a pleasant speaker, we could listen to him talking about wine for hours. The winery is beautiful, we tasted several wines together with delicious food. We are very glad we chose this activity during our stay in Siena.”

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11.Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch

★★★★★★★★★★5.0 · 103 reviews · 8 hours (approx.) · from $276

Explore Brunello wineries from Siena with cellar tours, tastings, a pairing lunch, Montalcino, and comfortable small-group transport.

“Two different winery tours/tastings where we learned all about the requirements and process of producing Beunello di Montalcino and other wines. The first was a broader tasting while the second included food/lunch with time to explore the town of Montalcino in between. Our drivers were super informative and very friendly.”

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