Siena

15 Best Siena Wine Tours

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.

1.Small-Group Brunello Di Montalcino Wine-Tasting Trip From Siena

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 was an AMAZING experience!! We spent all day tasting high quality wine at very small family vineyards and enjoying authentic Italian food made in their kitchens. Our guide, Mattia, was so great! He was knowledgeable (a wine-maker himself) and SO funny! Our group was…”

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3.Florence: Siena, San Gimignano and Chianti Small Group Tour

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

“The guides Davids Tony and Susy worked as a team to ensure we had a great time few laughs .very friendly and very informative. I enjoyed the unique history lesson as we went along.”

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5.From Siena: Brunello Di Montalcino Guided Wine Tour W/ Lunch

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

“Our day touring the wineries with Manu was excellent. The tour was wonderful, and the people we met at the wineries were friendly informative and of course the wine was sublime. Most of all our guide made the day lots of fun, he gave lots…”

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6.Wine Tour With Wine Tasting in Siena

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.”

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8.Small-Group Montepulciano and Pienza Day Trip From Siena

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

“It was a beautiful day from start to end. Our driver/tour guide, Guillermo , was fantastic in every regard: inteligent, knowledgeable, funny ,full of great energy and he brought us back safely to Siena. We could not ask for better guy. The tour itself was…”

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9.Siena: Pasta and Tiramisu Cooking Class With Wine

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

“This class was amazing. The teacher was so good at institutions. And we had a fun group to spend time with. Definitely worth the money. I’ll be able to cook these foods when I return home. Best part was eating with we prepared.”

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11.A Brunello Cooking Class With Vineyards View Winery

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

“This was the best day ever! We cooked 4x dishes (1x appetiser, 2x pasta, 1x dessert) and these were paired with 3 wines, plus we had a 4th wine while we cooked! Cooking and having lunch overlooking the winery was magical! The castle/fortress tour was…”

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13.Siena: Educational Wine Tour & Tasting

Open the door to a world where tradition and innovation blend seamlessly - discover the hidden gem that makes this tour truly exceptional!

★ 5.0

“Absolutely excellent tour. Our guide Maya was very knowledgeable about wine making and a lovely girl and very funny. Our meal was absolutely delicious and the wine tasting was excellent and great fun. I would highly recommend this tour. Certainly, it is not to be…”

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15.Chianti and Castle Small Group Tour From Siena With Wine Tasting

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

“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.”

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4.5San Gimignano, Chianti, and Montalcino Day Trip From Siena11 hours (approx.)$168.96 4.9From Siena: Chianti Farm Cooking Class$130.28 4.0Vespa Tour With Lunch&Chianti Winery From Siena$168.36 5.0Tuscany Hiking Tour From Siena Including Wine Tasting4 hours (approx.)$72.56 5.0Organic Winery Tour and Wine Tasting in Siena2.5 hours$88 5.0Brunello Di Montalcino Wine Tour of 2 Wineries With Pairing Lunch8 hours (approx.)$276.95 5.0Walking Tour of Siena With Food & Chianti Wine2 hours 30 minutes (approx.)$97.66 4.0From Siena: Pienza and Montepulciano Wine Tour9 hours 30 minutes (approx.)$154.98 4.0From Siena/Chianti: Dinner & Drinks in the Chianti Vineyards$123.48 4.5Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle1 hour 30 minutes (approx.)$71.23 5.0Full-Day 2 Wineries Tour in Montepulciano With Tasting and Lunch6 to 8 hours (approx.)$265.49 5.0Wine Tasting at the Winery in the Panoramic Terrance1 hour (approx.)$33.79 5.0Small-Group Chianti Trip With Wine Tasting From Siena8 hours (approx.)$217.22 5.0Chianti and San Gimignano – 2 Wineries With Pairing Lunch$423.77 5.0Siena: Winery Tour, Wine Tasting and Lunch2.5 hours$77 4.8From Siena: Chianti and San Gimignano Sunset Tour$203.91 4.0Half-Day Brunello Di Montalcino Wine Tour From Siena5 hours 30 minutes (approx.)$142.97 5.0Small-Group Chianti and San Gimignano Sunset Trip From Siena8 to 9 hours (approx.)$217.23 4.0Tuscan Chianti Hills Horseback Riding Tour1 hour 30 minutes (approx.)$90.11 4.4Badesse: Vespa & Chianti Tour in the Tuscan Hills$123.48 4.5Montalcino: Brunello Wine Tasting Experience1 hour 30 minutes (approx.)$39.05 4.7Siena: Balloon Flight Over Tuscany With a Glass of Wine$351.18 4.5Vintage Fiat 500 Tour From Siena: Tuscan Hills and Winery Lunch$191.58 5.0Guided Winery Tour and Wine Tasting in Siena2 hours 30 minutes (approx.)$90.51