6 Wine Tasting Tours in Siena Worth Booking

1.Chianti and Castles Tour with Wine Tastings

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

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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2.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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3.Tuscany Hiking Tour from Siena Including Wine Tasting

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

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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4.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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5.winery tour, wine tasting and lunch

★★★★★★★★★★5.0 · 70 reviews · 2.5 hours · from $77

Spend 2.5 hours at family-run Winery San Giorgio a Lapi with guides such as Jesse, Gabriele, and Giuseppe. Walk through Chianti vineyards to a medieval church with Nasini frescoes, tour the cellar, then taste estate wines with a generous Tuscan lunch on a panoramic terrace.

“The tour was amazing! We started by having a walk through the property and some explanation about wine making. We got to see all the steps that take to make the wine. Our guide Jesse was chatty and funny, and really made us feel comfortable. We were a group of 6 people and it was perfect. The lunch was amazing! We were given a proper sit down meal and not just some snacks! And of course the wine tasting was great as well, we could choose from 2 different wines in each round. If you’re going with someone else, I suggest you both choose one of each so this way…”

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6.Tour and Wine Tasting in a Tuscan Private Castle

★★★★★★★★★★4.9 · 50 reviews · 2 hours · from $51Best value

At Castello Poggiarello, Elena or Sveba leads you through the castle, Renaissance gardens, 16th-century chapel, and organic winery. You will taste about four or five wines with water and a snack. The two-hour tour runs in Italian, English, or French and includes parking.

“The tour was excellent. Elena is very passionate about the castle and the wine. It was really nice to learn about the castle and the property. The wines were lovely and not typical of the region. It was a great wine tour that was unconventional and not a cookie cutter experience. Thank you for a wonderful afternoon, Elena!”

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