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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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

“Wonderful trip through Tuscany with beautiful scenic views, stops at two charming Tuscan towns, and a delicious meal at a farm. Our guide Billy was very informative and a lot of fun. He went out of his way to make sure I could join the…”

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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 had an amazing afternoon on this tour. We arrived and had a brief tour of the castle and wine making areas, and then the real fun started with the cooking class. Adriana was such a fun chef, she was kind and funny and taught…”

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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

“We had such a wonderful time on this tour! Valesca and Luigi were the best! Valesca speaks fluent Italian, English and Spanish and was extremely pleasant and kept the group running on time. The wineries were excellent. The two towns were amazing. Luigi was a…”

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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

“this was a very enjoyable tour. Our guide was excellent. The winery tasting and lunch was delicous.. Highly recommend this tour to everyone, especially wine lovers.”

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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

“Our driver was very helpful and his driving was good. Had a great time even in very heavy rain. Wine tastings with lunch were great.”

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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

“What an excellent way to see Chianti I on a Vespa! Fredricho was an excellent guide leading us and stopping @ 3 towns allowing plenty of time to sightsee, shop, and experience the local atmosphere. Stopping @ Casale Dello Sparviero Winery was amazing! Jada was…”

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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

“Great tour of Tuscany, great selection of wineries that offer excellent Brunello wines from the Maltucino region. Driver was very knowledgeable about Tuscany region and the wines”

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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

“Our tour guide Mohad was incredibly knowledgeable, not only about Siena’s history but also about all the food, wine and gelato places. Some of them truly hidden gems! Perfect mix of walking tour and tasting of local specialties, all within 3 hours and away from…”

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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

“The towns and wine tasting experiences were good. The tour guides were friendly, informative and patient. However, the transport vehicle was substandard, with broken seat backs, and inadequate shocks which was especially problematic when we hit speed bumps. Returning down steep roads, mechanical noises (perhaps…”

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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.