Here are the wine tours I’d book out of Siena, covering Chianti Classico, Brunello di Montalcino, and Vino Nobile country. All three zones sit within about an hour of the city. Most trips pair two estate visits with a proper cellar tasting and lunch.
Join us for a luxurious small-group wine-tasting adventure in Montalcino. Experience the rich flavors of Brunello di Montalcino wine in the heart of Tuscany.
Most Popular★ 5.0“This tour was a wonderful experience! We visited three distinct wineries and tasted a variety of Rosso and Brunellos. We had a great lunch that was homemade in the family kitchen. The drive was beautiful and Emanuel, our “professional drive” (as he calls himself), is…”
★★★★★★★★★★
952 reviews9 hours (approx.)From $217.67by Tuscan Escapes by Papilio SRL
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Discover the enchanting castles and exquisite wines of Chianti on a captivating tour from Siena. Indulge in unforgettable tastings and experience Italian elegance like never before.
★ 4.6“It was excellent and well-timed. Great value for the money!”
★★★★★★★★★★
631 reviews5 hoursFrom $100by My Luxury Drive
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Wander through the enchanting landscapes of Tuscany on the Florence: Siena, San Gimignano, and Chianti Small Group Tour, where hidden gems and unique experiences await...
★ 4.9“Excellent! Just the right mix of history, food and wine and free time to enjoy the beautiful cities. Truly amazing tour!”
★★★★★★★★★★
433 reviews9 hoursFrom $175by Prestige Rent - Tours in Italy
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Keen to unravel the mysteries of Chianti wines?
★ 4.9“Ilaria is a great passionate guide. She made us a tour of the vineyard and the cellar with clear and lively explanation. Also mentioned some interesting information regarding organic farming. Tasting was great with some food and generous servings. Just a note : no discount…”
★★★★★★★★★★
430 reviews2 hoursFrom $47by Fattoria di Montemaggio
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Discover the prestigious Brunello Di Montalcino wine on a guided tour from Siena. Indulge in a delicious lunch, explore vineyards, and savor the rich flavors.
★ 4.9“Nothing bad to say. We enjoyed this trip more than any other. Our guide had a very personable personality and each stop was truly memorable. Highly recommended.”
★★★★★★★★★★
357 reviewsFrom $203.91by Tuscan Escapes by Papilio
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Discover the enchanting flavors of Siena on a wine tour like no other. Indulge in exquisite wine tastings and immerse yourself in the beauty of this Tuscan gem.
★ 5.0“Informative tour of an organic winery; so much to learn about what goes into making a good, organic wine. The wine was delicious and so was the lunch. The grounds are beautiful and picture postcard worthy.”
★★★★★★★★★★
352 reviews3 hours (approx.)From $102.84by Az. Agr. La Lastra
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Curious about the hidden gem in Val D'Orcia?
★ 4.1“One of the best Italian trips I’ve ever been to. To be honest I’m not a fan of wine but the wine provided is good and the cheeses/olive oil/salami are some of the best. Talking about the main travel, you’ll have time to take enough…”
★★★★★★★★★★
323 reviewsFrom $146.14by My Tour in Italy
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Discover the charm of Montepulciano and Pienza on this unforgettable day trip. Explore the stunning landscapes, taste exquisite wines, and indulge in mouthwatering local delicacies.
★ 5.0“Absolutely wonderful tour. Tour guide exceptional. Julianna was very informative kind and fun to be with. Loved seeing the countryside and the villages. Best tour I’ve been on with 8 folks. Loved the small group.”
★★★★★★★★★★
281 reviews8 hours (approx.)From $217.77by Tuscan Escapes by Papilio SRL
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Join a delightful culinary journey in Siena, where you'll master pasta and tiramisu; discover what awaits in this unforgettable cooking class experience.
★ 4.8“Basic cooking class suitable for everyone, we made pasta, ravioli, gnocchi and tiramisu.”
★★★★★★★★★★
274 reviews3 hoursFrom $81by The Roman Food Tour
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Join our Siena Wine Tasting Class in 2024! Don't miss out on canceling 24H prior for a full refund. Discover the art of wine tasting today!
★ 5.0“Terrific class. Had a ton of fun. So convenient being in the city walls. Drank, laughed and learned a great deal. Manuel was a terrific teacher and good natured person. No pressure sale. If you don’t know much about wine from Tuscany, want to learn…”
★★★★★★★★★★
264 reviews2 hours (approx.)From $72.59by Papilio srl
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Discover the art of Italian cuisine at our Brunello Cooking Class with breathtaking vineyard views. Unleash your inner chef and indulge in a truly immersive culinary experience.
★ 5.0“Our cooking instructor was wonderful, and very patient! The view for cooking and the meal was amazing.”
★★★★★★★★★★
221 reviews4 hours (approx.)From $313.35by Forzoni Tours
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Immerse yourself in the essence of Tuscany's charming towns on a small-group tour from Siena, where authenticity meets luxury in an unforgettable experience.
★ 4.9“Our guide was excellent and the tour was a wonderful way to explore. The farm we went to for lunch was amazing!”
★★★★★★★★★★
220 reviewsFrom $203.91by Tuscan Escapes by Papilio
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Open the door to a world where tradition and innovation blend seamlessly - discover the hidden gem that makes this tour truly exceptional!
★ 5.0“It was amazing! Very informative the wines were incredible! The owner of the winery explained every detail and you could tell he was very passionate about his craft.”
★★★★★★★★★★
203 reviews3 hoursFrom $100by Azienda Agricola La Lastra
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Journey into the heart of Tuscany for a tantalizing blend of culture, history, and wine tasting - where every sip and sight leaves you craving for more.
★ 4.6“Beautiful tour and wine tastings. Luca our guide was great. Small group of 8 was perfect. about 9 hrs with lunch. Great value.”
★★★★★★★★★★
195 reviewsFrom $158.60by My Luxury Drive
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Explore the enchanting Chianti region on a small group tour from Siena. Immerse yourself in the beauty of castles and indulge in wine tasting. Book now!
★ 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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