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“This tour was beyond what I had expected. It was a memorable experience with a small group. We visited 3 different wineries, each had excellent selection of wines. We could see the cellars, they explained us the wine making process in depth. Our minivan driver…”
★★★★★★★★★★
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“This tour was amazing! I can’t say enough good things about this place! The tour was rich with knowledge of the winery itself and the history behind the region and the wine. We can’t wait to share our experience with our friends back home as…”
★★★★★★★★★★
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“I'm so glad I chose to book this at the last minute. La Lastra winery is stunning and picturesque, just what I pictured when I planned a visit to Tuscany. Maya was a knowledgeable and warm guide who gave us lots of engaging information about…”
★★★★★★★★★★
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“Guiliana is an expert guide, making our trip so interesting. She is an absolute rock star! She knew so much history about the area and answered any questions we had. The views through the winding roads on our trip to Pienza and Montepulciano were spectacular.…”
★★★★★★★★★★
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 had only two couples in this tour. One was from a combined food and wine tour and us, who were supposed to be just in the wine class. It was All Saints Day and things weere supposed to be winding down in Siena. Since…”
★★★★★★★★★★
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“From our tour of the winery to our cooking….SO great. We learned about the winery, cooking techniques……then put the food and wine together for a really great experience!”
★★★★★★★★★★
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“The tour was fantastic! Loved both wineries and the stops in the villages. Worth every penny! Our tour guide was great.”
★★★★★★★★★★
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 tour helped us see three towns when we had a short few days in Florence! Our guide Fabi was fantastic and walked us through each area carefully. We had insight into each area and a lovely wine tasting with a small accompanying lunch. Best…”
★★★★★★★★★★
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“It was fun & and enjoyable. Learned how to make pasta & tiramisu. Guide was excellent! Be prepared for lunch following lesson. Hope you like wine!”
★★★★★★★★★★
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, Giovanni, was prompt and provided a clean vehicle but he was NOT a guide as the trip was advertised. Rather than talk about Italy, he wanted to engage about politics and his heavy smoking between stops made the van stink. Our tour left…”
★★★★★★★★★★
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“It was great fun for our kids and us! Super way to see the country side. Lunch was very light just a meat and cheese board. Very young guides.”
★★★★★★★★★★
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“Fabulous! Great guide, perfect weather (late October), great like minded group of hikers. Was a good few hours (almost 4) of hiking but fairly flat and not a fast pace. Definitely recommend. The town of Monterriggioni at the end was the icing on the cake.”
★★★★★★★★★★
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“I booked this tour based on the reviews I'd read here, expecting a personalized, custom feeling experience. I expected wineries that I couldn't otherwise find, an engaged tour guide, and a generally great day. While the tour technically included all the pieces in the listing,…”
★★★★★★★★★★
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“Off the beaten track….where locals find the best pasta,gelato and vino. Ancient tomb attached to an enoteca. Minimal historical information but learn about the 17 contrada and life as a resident Guide Morad 5 STARS”
★★★★★★★★★★
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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