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

“Put up shades on the roof! Other than that it was a lovely time. We learned a lot- loved the black rooster story! The wine was delicious, the winery is beautiful. It is a challenge to get to- narrow roads, twisty turns, and large rain…”

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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

“Our guide, Marco, is very knowledgeable, personable and friendly. He shared a wealth of information with our group and answered all of our questions. The van was comfortable and Marco made it a very comfortable drive. It was wonderful to see the countryside and views,…”

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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

“Milo took us on a journey through history, culture and taste sensations. The exploration of wine characteristics and categories was engaging and conducted with much laughter and fun. It was certainly an enjoyable couple of hours and I would highly recommend putting this adventure on…”

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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 a wonderful winter cooking class with beautiful food, instruction and an incredible view over the Tuscan countryside. Add in some delicious wine and it was perfect.”

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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

“Valeska was a wonderful tour guide and both tastings were great! We had thought about going to a couple of vineyards on our own but it was well worth the little bit extra for the tour. I definitely recommend it.”

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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 wonderful addition to our trip to Italy. San Gimignano really is the postcard of Tuscany - the walls are amazing, the architecture is beautiful, the churches are astounding, and the gelato was to die for! Monteriggioni is a small but lovely fortress-town,…”

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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

“I am glad I read some of the other reviews prior to going on this tour. I feel like the reviews are accurate. This is a good tour. I wouldn't call it anything special. The tour guides do not do any training on the Vespa…”

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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

“The tastings and views were amazing. Very knowledgeable staff at the wineries provided a terrific introduction into rossos, Brunellos, and other wines produced in the Montalcino region.”

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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

“These two prominent mountain towns were an incredible experience. The guides did a good job setting it up and getting us there. Just the right amount of free time. The large production winery was unimpressive. I prefer small family production wineries.”

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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.