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

“Manu was an amazing guide, knowledgeable and hilarious. Wineries were intimate and top notch! Had the best time!!”

952 reviews9 hours (approx.)From $217.67by Tuscan Escapes by Papilio SRL

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2.From Siena: Chianti and Castles Tour With Wine Tastings

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

“Sara was our driver and she was fantastic! She was very friendly and attentive. We thoroughly enjoyed this trip and both of the tastings. The scenery alone was well worth the trip!”

631 reviews5 hoursFrom $100by My Luxury Drive

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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

“Excellent in every way. Marco had great energy, made us laugh and taught us a lot about Tuscany and Tuscany wines. The three wineries were all a little different and all great.”

357 reviewsFrom $203.91by Tuscan Escapes by Papilio

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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

“Delicious light lunch is served along with generous pours of red and white organic wines. Maia was knowledgeable on the vineyard and the process of making organic wines.”

352 reviews3 hours (approx.)From $102.84by Az. Agr. La Lastra

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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

“This was our last tour and probably my best and favorite. Our guide was Bill/William He was a wealth of information and was so friendly and kind. I highly recommend this tour and this guide. Don’t forget to tip your guides when your done. They…”

281 reviews8 hours (approx.)From $217.77by Tuscan Escapes by Papilio SRL

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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…”

221 reviews4 hours (approx.)From $313.35by Forzoni Tours

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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 an amazing afternoon of touring the Tuscan region with Valeska as our fun tour guide and Mohammed as a very safe driver! The 2 wineries were informative and the guides at the wineries were interactive, personable, and taught us so much about wines.…”

172 reviews5 hours (approx.)From $59.13by myTour in Italy

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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