The 11 Best Siena Drinks Tours

1.San Gimignano, Siena, and Chianti Wine Tour

★★★★★★★★★★4.5 · 3,762 reviews · from $164Our pick

Spend nine hours touring Tuscany by air-conditioned minibus, with time in Siena, a Chianti estate, and San Gimignano. Expect five wine tastings, olive oils, balsamic vinegar, and a traditional lunch. Guides such as Marco, Lyla, Marta, and Enrieta are praised for keeping the day friendly and on time.

“Marco our tour guide was amazing! He was very knowledgeable and explained everything clearly. He also made sure to talk and connect with many of the people on the tour individually, so it felt very personalized! The tour itself was also incredible - being able to see all the beautiful areas that I did in one day? 10/10”

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2.Chianti and Castles Tour with Wine Tastings

★★★★★★★★★★4.6 · 631 reviews · 5 hours · from $100

Travel in a small group of up to eight from Siena through Chianti’s vineyard country. Your guide, possibly Fabio, Daniel, Sara, or another multilingual driver-guide, takes you to Castellina, Monteriggioni, two wineries, scenic viewpoints, and tastings of wine, olive oil, balsamic, and Tuscan snacks.

“Fabio was an excellent tour guide with great insight into the region and a good sense of humour. Fabio took us around the Chianti area countryside safely and expertly and made our visit to the region an enjoyable one. Thank you Fabio, you were excellent !!”

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3.Total Immersion Wine Tour in Chianti

★★★★★★★★★★4.9 · 430 reviews · 2 hours · from $47Best value

At Fattoria di Montemaggio, guides Francesco, Stefano, and Ilaria lead a two-hour visit through vineyard and cellar. You’ll learn organic Chianti Classico methods, taste five estate products, sample olive oil and local foods, and finish with a mini wine-tasting lesson and optional grappa.

“The knowledge of the guide and the depth he went to in explaining the process.”

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4.Brunello di Montalcino Guided Wine Tour W/ Lunch

★★★★★★★★★★4.9 · 357 reviews · from $203

Travel from Siena in a small minivan to three Brunello wineries, the hill town of Montalcino, and Sant’Antimo Abbey. English-speaking guides such as Marco, Georgia, Paolo, and Giulia lead tastings, cellar visits, and a family-run winery lunch during this nine-hour day.

“The Brunello di Montalcino guided wine tour was amazing. Dan our guide was excellent! We were so lucky to get him as our guide. He picked beautiful vineyards to show us and the lunch was outstanding!! We purchased several bottles of wine from each vineyard where they conveniently shipped them to our home in the USA. I highly recommend this tour it is not to be missed.”

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5.A Brunello Cooking Class with Vineyards View Winery

★★★★★★★★★★5.0 · 221 reviews · 4 hours (approx.) · from $313Top rated

Spend about four hours at Castello Tricerchi near Montalcino, making filled pasta, pici, and a Tuscan dessert with a chef such as Alexandra or Jacomo. Tour the winery and cellar, then eat your meal with Brunello and Rosso di Montalcino on a terrace above the vines.

“Amazing Experience! There was so much food and wine that we left uncomfortably full but happy. The recipes were simple to make and delicious. The chef was very friendly, knowledgeable, welcoming and fun to cook with.”

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6.San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

★★★★★★★★★★4.5 · 171 reviews · 11 hours (approx.) · from $95

From Florence, you’ll visit San Gimignano, Monteriggioni, Siena, and a Chianti winery with an English-speaking escort. Expect free time in the towns, a three-course Tuscan lunch, three Chianti wines, olive oil, balsamic vinegar, and vin santo. Guides such as Marta and Sandro are often praised for clear local tips.

“The wine tasting and lunch was the best part. We really enjoyed the whole day as a whole. The guides were very helpful”

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7.Vespa Tour with Lunch&Chianti Winery from Siena

★★★★★★★★★★4.0 · 126 reviews · from $168

Ride a Vespa in convoy from Siena through Chianti, with stops in Castellina, Radda, and Monteriggioni. You can drive if you have real scooter experience and an international license, or ride as a passenger. The day includes a winery visit, wine tasting, and a light Tuscan lunch.

“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.”

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8.Tuscany Hiking Tour from Siena Including Wine Tasting

★★★★★★★★★★5.0 · 112 reviews · 4 hours (approx.) · from $72

Meet your guide at Siena station for an easy 7 to 8 kilometer walk along the Via Francigena. Guides such as Keko, Giovanni, Francesco, and Alessia explain local history, plants, and rural life before a two-wine tasting in Monteriggioni. Return independently with the included ticket.

“Great hike. Our guide, Giovani was was well prepared and very knowledgeable. Easy hike. No special gear required except hiking shoes or runners. Pilgrim's trail is very engaging. Wine tasting was excellent. Well worth the money”

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9.Organic Winery Tour and Wine Tasting

★★★★★★★★★★5.0 · 111 reviews · 2.5 hours · from $88

Spend 2.5 hours at Azienda Agricola La Lastra, an organic winery about 2 kilometers from Siena. Guides such as Maia, Mya, and Gianluigi explain vineyard care, cellar work, and wine tasting before pairing five wines with seasonal Tuscan food and garden vegetables.

“The tour provided by Maia was incredible. She is both knowledgeable and professional, while being simultaneously engaging. Her passion for organic viniculture was contagious, and we cannot wait to taste more of this fine Tuscan wine. Thank you so very much.”

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10.Brunello di Montalcino Wine Tour of 2 Wineries with Pairing Lunch

★★★★★★★★★★5.0 · 103 reviews · 8 hours (approx.) · from $276

Travel from Siena in a luxury air-conditioned vehicle to two boutique Brunello wineries, with cellar visits, tastings, a three-course pairing lunch, and time in Montalcino. Guides such as Niccolò, Stefano, and Luigi add local wine knowledge, though the exact stops can vary.

“Thank you very much Nicolo for the best wine tour ever. We enjoyed both vignards, the food was excellent.”

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11.Day Tour in a Vintage Fiat 500 with Winery

★★★★★★★★★★4.4 · 41 reviews · from $146

Drive an original manual Fiat 500 from Siena through the Chianti hills, stopping at Castellina and a countryside winery for wine and dry snacks. Guides such as Lorenzo, Francesco, Gabriele, and Sam add local stories. Drivers need a license and credit card for the rental deposit.

“It was really wonderful, sam was the perfect guide for showing us around the beautiful toskana”

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