Siena

15 Best Siena Wine Tours

The wine country at Siena’s gates: Brunello tastings in Montalcino, Chianti immersions and the Montepulciano-Pienza loop with pecorino between cellars. Three of Italy’s greatest reds grow within an hour; the designated driver comes included.

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

Discover authentic Brunello di Montalcino wines on this small-group day trip from Siena, including visits to three charming wineries, a Tuscan meal, and the Abbey of Sant'Antimo.

Most Popular★ 5.0

“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…”

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2.Total Immersion Wine Tour in Chianti

Experience authentic organic Chianti wines with stunning vineyard views, expert guides, and delicious local snacks on this immersive two-hour tour in Tuscany.

★ 4.9

“Francesco was amazing—very knowledgeable, friendly, and funny, the perfect person to guide us around the vineyard. We tasted some incredible wine and had a wonderful time. This is a special place that will always stay in our hearts. Highly recommended!”

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3.Siena: A Wine Tour and Tasting Experience

Discover Tuscany’s wine heritage with a small-group tour from Siena. Taste organic wines, learn from a passionate guide, and enjoy a scenic countryside lunch.

★ 5.0

“It was lovely. I missed my scheduled time (11:30am) - caution getting a taxi from Siena can be challenging- so I joined the 4pm tasting. Our host Maya was great. Funny, honest and clearly passionate about what she does. My group was friendly. Wine was…”

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4.Small-Group Montepulciano and Pienza Day Trip from Siena

Discover the charm of Tuscany with this small-group day trip from Siena to Pienza and Montepulciano, including wine tastings, a cheese farm, and stunning scenery.

★ 5.0

“We had a wonderful day with our amazing and awesome guide, Daniele. He was extremely knowledgeable and informative and personable. He shared bits of history and interesting facts about the area. His knowledge of wine and it’s production is impressive. He’s a true connoisseur of…”

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5.Wine Class – Tuscan Classics

Discover Tuscan wines through an engaging 2-hour class in Siena, learning from local experts, tasting regional wines, and pairing with delicious bites.

★ 5.0

“Wine class with Milo was great. Learned a lot about wines from Tuscany and the history behind them. Tasted some great local Tuscan wines. Highly recommend this class before you go on vineyard trips.”

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6.A Brunello Cooking Class with Vineyards View Winery

Experience a hands-on Brunello wine region cooking class on a scenic Tuscan vineyard terrace, combined with castle tours and wine tasting near Siena.

★ 5.0

“We took this tour and cooking class with 'Tours of Tuscany' and our entire group agreed it was a top moment of our entire Italy trip! The property where you take the class is one of a kind; a historic building and winery in the…”

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7.Chianti and Castle Small Group Tour from Siena with Wine Tasting

Discover Tuscany’s best with this small group Chianti and castle tour from Siena, featuring visits to two wineries, picturesque villages, and stunning views.

★ 4.5

“You’ll have to get transportation to the meeting point. Make sure to wear walking shoes and check the weather. Guides are knowledgeable and friendly. Highly recommend for groups or even if traveling solo!”

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

Discover Tuscan charm on this full-day tour visiting San Gimignano, Siena, and Monteriggioni with wine tastings, lunch, and expert guides from Florence.

★ 4.5

“Our tour guide Aaron was awesome!!! Very patient and informative!!! The winery was awesome!!! Loved the food, wine and our host! Our tour guide in Siena was very nice but talked too fast so we couldn’t understand a lot of her tour. Overall, loved the…”

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

Discover Tuscany’s highlights on this small-group day trip from Siena, including San Gimignano, Montalcino, and Chianti wine tastings—perfect for wine lovers and history buffs alike.

★ 4.5

“Montalcino was not worth a stop. Brunello wine was good but host’s English was not good enough. The stop at Poggio Al Laghi Was good. Driver was very nice and accommodating.”

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11.Vespa Tour with Lunch&Chianti Winery from Siena

Experience Tuscany's scenic beauty on a Vespa from Siena, visit a Chianti winery, enjoy wine tasting, and savor a light lunch in this full-day adventure.

★ 4.0

“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…”

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12.Tuscany Hiking Tour from Siena Including Wine Tasting

Explore Tuscany on this scenic half-day hike from Siena, including a walk along the historic Via Francigena and a delightful wine tasting in Monteriggioni.

★ 5.0

“Great hike. Our guide, Giovani was was well prepared and very knowledgeable. Easy hike. No special gear required except hiking shoes or runners. Pilgrim's trail is very engaging. Wine tasting was excellent. Well worth the money”

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

Discover Tuscany’s finest Brunello wines on this small-group tour visiting two historic wineries with tastings, scenic drives, and a delicious pairing lunch.

★ 5.0

“This tour was amazing! It was nice to visit some smaller wineries in Montalcino and hear about their wine making process. All of the wines were amazing, and the lunch was spectacular as well. The quick stop in the historic center of Montalcino was the…”

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14.Siena walking tour with lunch & Chianti wine

Discover Siena’s charm on a guided walking tour with authentic Tuscan food, regional wines, and hidden sights—perfect for lovers of history and cuisine.

★ 5.0

“I recently had an amazing walking tour of Siena, and I can’t recommend it enough! Our guide was incredibly knowledgeable and truly a joy to be with, making the experience both informative and enjoyable. The city is stunning, and exploring it on foot allowed us…”

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15.Tuscany Wine & Hills from Siena

Discover Tuscany's charm on this full-day Siena-based tour featuring visits to Pienza and Montepulciano, with wine tastings, stunning views, and free time.

★ 4.0

“I was not impressed with this tour. The pic with the promo is not what you get. The tour guide was very professional and informative. But, this was not a Tuscan wine tour, far from it. The wine tasting was in a sterile wine factory.…”

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More Siena Wine Tours

5.0Full-Day 2 Wineries Tour in Montepulciano with Tasting and Lunch6 to 8 hours (approx.)$265.49 5.0“CLASSIC” Wine Tasting and Typical Tuscan Products1 hour (approx.)$33.79 5.0Small-Group Chianti Trip with Wine Tasting from Siena8 hours (approx.)$217.22 5.0Chianti and San Gimignano – 2 Wineries with Pairing Lunch$423.77 5.0Siena: winery tour, wine tasting and lunch2.5 hours$77 4.0Small group Brunello di Montalcino Wine Tour from Siena5 hours 30 minutes (approx.)$142.97 5.0Small-Group Chianti and San Gimignano Sunset Trip from Siena8 to 9 hours (approx.)$217.23 4.0Tuscan Chianti Hills Horseback Riding Tour1 hour 30 minutes (approx.)$90.11 4.5Montalcino: Brunello Wine Tasting Experience1 hour 30 minutes (approx.)$39.05 4.5Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch$191.58 5.0Guided Winery Tour and Wine Tasting in Siena2 hours 30 minutes (approx.)$90.51 4.9Siena: Tour and Wine Tasting in a Tuscan Private Castle2 hours$51 5.0Siena Underground Wine tasting in a Medieval Cave1 hour 15 minutes (approx.)$90.11 4.0Vespa Tour in Chianti Small Group from Florence$167.68 4.8Montepulciano: Cinta Senese Tour With Food Tasting1.5 hours$65 5.0Guided tour of the cellars with wine tasting and lunch2 hours 30 minutes (approx.)$77.89 5.0Savor Siena Food and Wine Tour2 hours (approx.)$71.90 5.0Pienza, Val d’Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA8 hours (approx.)$527.24 4.0Montalcino Castle and Vineyards tour with tasting1 hour (approx.)$46.86 4.7Chianti: Wine and Olive Oil Tasting with Cellar Tour1 hour$41 5.0Small Group E-Bike Chianti Tour with farm lunch from Siena6 hours (approx.)$216.25 5.0Exclusive Wine Tasting in the Historic Center of Siena1 hour (approx.)$42.05 5.0Small group Chianti, Montalcino & Monteriggioni castle from Siena5 hours 30 minutes (approx.)$198.95 5.0Private Tour: Pienza and Montalcino Organic Cheese and Wine Tour8 hours (approx.)$840.98

Explore Siena

A striped Duomo, a shell-shaped square and Brunello next door.