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

“My husband and I recently spent a full-day wine tour around Siena that exceeded every expectation. We visited three distinct vineyards, enjoyed guided tastings at each, and savored a chef-prepared lunch at the second estate. The scenery, the wines, and the overall pacing of the…”

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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

“Franceso was great very passionate about the boutique vineyard & explained lots about the history & the area. Wines were delicious & purchases were made to enjoy during the rest of our holiday. Would highly recommend going!”

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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

“Found this wine and food tour and loved it. Beautiful setting in the winery. We toured the vineyard and cellars. Then the wine pairing!!! So good my husband bought a case to take away and one shipped home. Loved the fact that it was organic.…”

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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

“What a fun day! Our guide, Paolo, was wonderful. His knowledge of the Tuscan hills was extensive. He could answer any questions we threw at him. His driving skills were also impressive. The time flew by. We had a great bunch of travelers in our…”

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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

“We learned a lot about the region and the different wines. Portions were very generous for tasting. The variety of wines was great.”

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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

“Wow! There are no words to describe this tour, but I will try! The setting gorgeous The vineyard beautiful The cooking class- What a wonderful experience, we had never made handmade pasta before! It came out good and it was so delicious! The wine- well…”

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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

“This wine tour is amazing , our guide was friendly and interesting We recommend a small group tour Great scenery great vino great day Not to be missed”

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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

“Sandro went above and beyond. He loves his work and it shows. The information provided was perfect. The tour itself was great definitely worthwhile. Sandro really went out of his way to help me since I wasn’t able to walk alot”

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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

“We had a fantastic day with tour driver Fabio who exceeded our expectations with great commentary & stopping for photos. Fully recommend this Day trip.”

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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 Vespa ride through the country side was pretty cool. They dropped us off in some towns and didn’t show us around. Also did not explain further. Not much of a tour in that regards. **** Only sign up for Vespa ride if you have…”

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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

“Our guide shared impressive knowledge of the history and nature of the area. Comfortable pace and delightful wine tasting experience at the end.”

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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

“Julie was fantastic as a tour guide, extremely knowledgeable and very pleasant during the whole tour. As a US citizen she was also able to compare living in the US vs living in Siena, which was very interesting!”

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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

“Signed up for a minibus tour six months ago. Ended up on a full tour bus. Stopped at one winery.the entire day. “Snacks” were a packet of saltine crackers. I guess I misread the description? Enjoyed the other people on the bus and the towns…”

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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.