Italy · WINE TASTINGS IN SIENA

The 11 Wine Tastings in Siena That Earn Their Price

11 tours  ·  from $47 a head

This is the shortlist you would send a friend: 11 wine tastings in Siena worth the money, each with its price, its traveller verdict and the one thing to know before you commit.

From Florence: San Gimignano, Siena, and Chianti Wine Tour - Siena: grand squares, narrow lanes, and a tight clock
Siena Tours, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Siena

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

1.San Gimignano, Siena, and Chianti Wine Tour

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

Explore Siena, Chianti, and San Gimignano from Florence with wine, Tuscan lunch, free time, and an air-conditioned ride.

“12 hours very well splited which led to beautiful memories. We were lucky to have Marta as a guide. She shared with us the history of the region and some old legends. Sienna, Colle di Val d’Elsa and San Gimignano worth for sure spending more than one day to feel them.”

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Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena - The first winery: vineyards, cellars, and an introduction to Brunello
Food & Drink, Siena Tours, Tour Reviews, Wine Tastings, Wine Tastings in Siena

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

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 Montalcino wineries, enjoy a homemade Tuscan lunch, visit Sant’Antimo Abbey, and return to Siena by minivan.

“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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From Siena: Chianti and Castles Tour with Wine Tastings - Castellina in Chianti and the appeal of a walled hill town
Siena Tours, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Siena

From Siena: Chianti and Castles Tour with Wine Tastings

3.Chianti and Castles Tour with Wine Tastings

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

Tour Chianti from Siena in a small van, visit Castellina and Monteriggioni, and taste regional wines at two Tuscan wineries.

“Daniel was a fun informative guide . We visited beautiful little villages and 2 wonderful wineries with amazing views of the Chianti wine region .The wine we tasted was lovely and each winery gave us a different experience. Highly recommended.”

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Florence: Siena, San Gimignano and Chianti Small Group Tour - Meeting the minibus at 7:45 AM
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Florence: Siena, San Gimignano and Chianti Small Group Tour

4.Siena, San Gimignano and Chianti Small Group Tour

★★★★★★★★★★4.9 · 433 reviews · 9 hours · from $175

Spend a day in Tuscany visiting Siena, a family winery, and San Gimignano, with lunch, wine tasting, guided walks, and free time.

“Lorenzo was a fantastic tour guide and Alessio made the ride very comfortable. Such a great day well spent at a comfortable pace with a good amount of historical information and lots of free time to shop around and take photos.”

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Total Immersion Wine Tour in Chianti - Walking Through Organic Agriculture
Siena Tours, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Siena

Total Immersion Wine Tour in Chianti

5.Total Immersion Wine Tour in Chianti

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

Tour an organic Chianti winery, taste five estate wines, learn wine skills, and enjoy Tuscan views with cheese, salami, bread, and olive oil.

“the guide was very freindly and he really created an experience we will not forget.”

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From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch - Starting in Siena at San Domenico
Guided, Lunch Experiences, Siena Tours, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Siena

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

6.Brunello di Montalcino Guided Wine Tour W/ Lunch

★★★★★★★★★★4.9 · 357 reviews · from $203

Spend nine hours in Montalcino with three Brunello wineries, a family-run Tuscan lunch, Montalcino town, and Sant’Antimo Abbey.

“What a great tour! We visited 3 fantastic wineries and had the pleasure of trying several selections of their wines. And Georgia was a wonderful tour guide; very insightful, knowledgeable, and accommodating. We couldn't have asked for a better day.”

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Siena: A Wine Tour and Tasting Experience - Stop one: reading the vines at La Lastra
Food & Drink, Siena Tours, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Siena

Siena: A Wine Tour and Tasting Experience

7.A Wine Tour and Tasting Experience

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

Tour Siena’s organic vineyards, learn winemaking from grape to bottle, taste four wines, and enjoy a seasonal Tuscan lunch at La Lastra.

“Wonderful! A small group, the sommelier was informative and kind. The winery is beautiful and the meal was fantastic. 10/10 would go back!”

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From Siena: Tuscany Hills Wine Tour - The long road through Tuscany
Siena Tours, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Siena

From Siena: Tuscany Hills Wine Tour

8.Tuscany Hills Wine Tour

★★★★★★★★★★4.1 · 323 reviews · from $146

Spend a full day from Siena tasting Chianti and Nobile di Montepulciano wines while exploring Pienza, Montepulciano, and Tuscany’s hill roads.

“I had great time on this tour, met some amazing people and get to see Montelcino, Pienza and Montepulciano which are all amazing little villages. both of the wineries we visited were amazing in their own way, great wine to taste/purchase. the tour guide was amazing, so overall I received more than I paid for, amazing day out.”

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A Brunello Cooking Class with Vineyards View Winery - Touring the 13th-Century Castle and Wine Cellar
Cooking Classes, Siena Tours, Tour Reviews, Wine Tastings, Wine Tastings in Siena, Workshops

A Brunello Cooking Class with Vineyards View Winery

9.A Brunello Cooking Class with Vineyards View Winery

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

Cook pasta on a terrace above Montalcino vineyards, tour a 13th-century castle, and pair your meal with Brunello wine.

“This was an absolutely amazing experience. We are traveling in a group of six married couples celebrating our 40th birthdays. The castle is a quiet dream originally constructed in the 1200s a top a hill overlooking the Tuscan hills and vineyard. You can see Montalcino a few miles away on its hilltop as well. The cooking class is in a small rustic building with gorgeous windows overlooking the winery. A mom and daughter team led our cooking class, starting with tiramasu, beef and pasta, while being served Persecco. We had lunch outside on a terrace where we were served their delicious wine. This has been the highlight of our two…”

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Siena: Educational Wine Tour & Tasting - Walking through the organic vineyards
Food & Drink, Siena Tours, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Siena

Siena: Educational Wine Tour & Tasting

10.Educational Wine Tour & Tasting

★★★★★★★★★★5.0 · 203 reviews · 3 hours · from $100

Review of La Lastra’s three-hour organic wine tour near Siena, with vineyard lessons, four wines, seasonal Tuscan lunch, and practical tips.

“This was an amazing tour. Our guide was really great, very informative, friendly and knowledgeable about the vineyard. Walk a little into the olive orchard and the vineyard and did a little tour in the wine cellar. Had a great wine tasting of 4 wines but as people asked questions he gave us tastes of several other wines and the lunch was really good. All made on site with produce grown on site. This was just a great experience”

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Siena: San Gimignano, Chianti & Montalcino Small-Group Tour - San Gimignano and the city of fine towers
Siena Tours, Tour Reviews, Tours, Wine Tastings, Wine Tastings in Siena

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

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