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“We had a great experience. Our guide/driver was incredibly knowledgable being a former winemaker himself. Wineries had stunning views and excellent wines. There were even two stops to see a small town and beautiful church. Highly recommend!”
★★★★★★★★★★
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“The knowledge of the guide and the depth he went to in explaining the process.”
★★★★★★★★★★
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“Very educational, and with a good portion of humor! Everyone in the class received a portion of personal attention.”
★★★★★★★★★★
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“It was a wonderful tour. Luca was informative and had a great sense of humor. The wineries we visited were welcoming and the tasting great. I highly recommend this tour.”
★★★★★★★★★★
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“Great time, Marta and driver were excellent. Would recommend this tour. Had a great time. Just a long day.”
★★★★★★★★★★
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“I recently took a cooking class in Siena, and it was one of the highlights of my trip to Italy! The experience was warm, welcoming, and incredibly hands-on. We learned how to make fresh, homemade ravioli from scratch — from kneading the dough to creating…”
★★★★★★★★★★
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 enjoyed our day tour to the vineyards and the rides of Tuscany region !!! Highly recommended this tour if you have a few days to Siena or just one day to spare from Florence.”
★★★★★★★★★★
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“We had a very fun and knowledgeable tour guide who made the trip such a great time! It was such a beautiful ride and the wine was amazing! We would definitely do it again!”
★★★★★★★★★★
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“This was a very enjoyable trip. Stephanie our guide was very good and the trip had the group in two vans so we could be dropped off and picked up close to the centre of Siena and Sean Gimignano. Stephanie is very knowledgable on the…”
★★★★★★★★★★
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“Amazing! We loved all the wineries and the stop in Pienza!! We were the only two on the tour and it was very engaging!”
★★★★★★★★★★
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“Great local recommendations, very interesting information about the city, and delicious food and drinks. Morad is a great host, very friendly and knowledgeable.”
★★★★★★★★★★
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“Our guide Luca was very informative. The first winery we visited did not give us the attention we deserved. They took in another group and paid more attention to them. They left us with little time to visit the area. I would have liked to…”
★★★★★★★★★★
99 reviews9 hours 30 minutes (approx.)From $154.98by myTour in Italy
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