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“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…”
★★★★★★★★★★
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.…”
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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“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,…”
★★★★★★★★★★
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“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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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“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.”
★★★★★★★★★★
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“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.”
★★★★★★★★★★
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“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,…”
★★★★★★★★★★
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“This was one of the highlights of our 3 week trip Italy. Chef Simone was amazing. It is clear he loves what he does and the food was to die for.”
★★★★★★★★★★
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“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…”
★★★★★★★★★★
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“Giovanni was an excellent informative and entertaining guide. Autumn is a perfect time but bring layers for cool or windy days”
★★★★★★★★★★
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“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.”
★★★★★★★★★★
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“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…”
★★★★★★★★★★
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“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.”
★★★★★★★★★★
99 reviews9 hours 30 minutes (approx.)From $154.98by myTour in Italy
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