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 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…”

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4.Total Immersion Wine Tour in Chianti

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…”

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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

“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.”

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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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7.From Siena: Val D’Orcia Wine Tour

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…”

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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

“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.”

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10.Siena Wine Tasting Class – Cancel 24H Prior & Full Refund

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…”

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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

“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.”

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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

“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…”

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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