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…”
★★★★★★★★★★
952 reviews9 hours (approx.)From $217.67by Tuscan Escapes by Papilio SRL
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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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430 reviews2 hoursFrom $47by Fattoria di Montemaggio
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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.…”
★★★★★★★★★★
352 reviews3 hours (approx.)From $102.84by Az. Agr. La Lastra
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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…”
★★★★★★★★★★
281 reviews8 hours (approx.)From $217.77by Tuscan Escapes by Papilio SRL
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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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264 reviews2 hours (approx.)From $72.59by Papilio srl
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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…”
★★★★★★★★★★
221 reviews4 hours (approx.)From $313.35by Forzoni Tours
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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”
★★★★★★★★★★
172 reviews5 hours (approx.)From $59.13by myTour in Italy
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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”
★★★★★★★★★★
171 reviews11 hours (approx.)From $95.58by CAF Tour and Travel
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Experience authentic Tuscan flavors with a small-group cooking class in Siena. Learn to make pasta, pizza, and tiramisu at a charming Chianti farmhouse.
★ 5.0“Simone is excellent, the location puts you just outside of Siena in the country side. You just take a taxi from the city…. Excellent, Excellent.”
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162 reviews4 hours (approx.)From $139.13by myTour in Italy
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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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150 reviews11 hours (approx.)From $168.96by myTour in Italy
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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…”
★★★★★★★★★★
126 reviewsFrom $168.36by myTour in Italy
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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.”
★★★★★★★★★★
112 reviews4 hours (approx.)From $72.56by Tuscan Escapes by Papilio SRL
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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“Wonderful tour Great wines! Patrizia Cencioni wines were incredible! Book it!! Great Day trip from Siena!”
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103 reviews8 hours (approx.)From $276.95by Forzoni Tours
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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!”
★★★★★★★★★★
99 reviews2 hours 30 minutes (approx.)From $97.66by Moro Tuscany Tours
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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…”
★★★★★★★★★★
99 reviews9 hours 30 minutes (approx.)From $154.98by myTour in Italy
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