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“Giorgia was an excellent guide to the best wine we experienced in Italy! She was full of interesting facts and history of the region. It made the experience lively and educational. She made sure all in the tour were included in conversation and all of…”
★★★★★★★★★★
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“Francesco was totally lovely and really knowledgeable about wine and the Chianti region”
★★★★★★★★★★
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“It was lovely. I missed my scheduled time (11:30am) - caution getting a taxi from Siena can be challenging- so I joined the 4pm tasting. Our host Maya was great. Funny, honest and clearly passionate about what she does. My group was friendly. Wine was…”
★★★★★★★★★★
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“Wonderful trip through Tuscany with beautiful scenic views, stops at two charming Tuscan towns, and a delicious meal at a farm. Our guide Billy was very informative and a lot of fun. He went out of his way to make sure I could join the…”
★★★★★★★★★★
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“Wine class with Milo was great. Learned a lot about wines from Tuscany and the history behind them. Tasted some great local Tuscan wines. Highly recommend this class before you go on vineyard trips.”
★★★★★★★★★★
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 an amazing afternoon on this tour. We arrived and had a brief tour of the castle and wine making areas, and then the real fun started with the cooking class. Adriana was such a fun chef, she was kind and funny and taught…”
★★★★★★★★★★
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“We had such a wonderful time on this tour! Valesca and Luigi were the best! Valesca speaks fluent Italian, English and Spanish and was extremely pleasant and kept the group running on time. The wineries were excellent. The two towns were amazing. Luigi was a…”
★★★★★★★★★★
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 very enjoyable tour. Our guide was excellent. The winery tasting and lunch was delicous.. Highly recommend this tour to everyone, especially wine lovers.”
★★★★★★★★★★
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.”
★★★★★★★★★★
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“Our driver was very helpful and his driving was good. Had a great time even in very heavy rain. Wine tastings with lunch were great.”
★★★★★★★★★★
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“What an excellent way to see Chianti I on a Vespa! Fredricho was an excellent guide leading us and stopping @ 3 towns allowing plenty of time to sightsee, shop, and experience the local atmosphere. Stopping @ Casale Dello Sparviero Winery was amazing! Jada was…”
★★★★★★★★★★
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“A wonderful, interesting, easy hike throughout the Tuscan countryside with fascinating facts along the way.”
★★★★★★★★★★
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“Great tour of Tuscany, great selection of wineries that offer excellent Brunello wines from the Maltucino region. Driver was very knowledgeable about Tuscany region and the wines”
★★★★★★★★★★
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“The towns and wine tasting experiences were good. The tour guides were friendly, informative and patient. However, the transport vehicle was substandard, with broken seat backs, and inadequate shocks which was especially problematic when we hit speed bumps. Returning down steep roads, mechanical noises (perhaps…”
★★★★★★★★★★
99 reviews9 hours 30 minutes (approx.)From $154.98by myTour in Italy
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