7 Wine Tastings in Siena the Drive Pays For

1.Chianti and Castles Tour with Wine Tastings

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

Travel from Siena in a small van of up to eight people, with an Italian, English, or Spanish-speaking guide. Visit Castellina in Chianti, Monteriggioni, scenic viewpoints, and two wineries. Tastings include Chianti wines, Tuscan snacks, and at some stops, olive oil and balsamic vinegar.

“Our guide was friendly and informative, we had brief stops at two Chianti villages and two wine tasting sessions, the second one was a sit-down with tastings of wines, oils and balsamics…the host was excellent company.”

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2.A Wine Tour and Tasting Experience

★★★★★★★★★★5.0 · 352 reviews · 3 hours (approx.) · from $102Top rated

Spend about three hours at Azienda Agricola La Lastra outside Siena, learning how organic grapes become wine, tasting four organic wines, and sharing a seasonal light lunch with wine and olive oil. Guides such as Maia make the technical side friendly and easy to follow. Small groups are capped at 12 people.

“Great, host was most informative, friendly and took time to answer questions. Tasted four organic wines and lunch. So much fun, would definitely do it again.”

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

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

Spend about 11 hours touring Tuscany from Florence, with free time in San Gimignano, Siena, and Monteriggioni, plus a winery visit, three-course lunch, and three Chianti wines. Guides such as Marta, Sandro, and Riccardo are praised for clear local context. Expect lots of walking and a potentially large group.

“Freddy did a wonderful job guiding 87 people on these tours. He was so kind and patient. San G was as beautiful as I hoped. I wish we had more time there! Siena was also just as beautiful! I would recommend this tour and experience for anyone! Freddy was spot on with his recommendations in each village!!!”

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4.Tuscany Hiking Tour from Siena Including Wine Tasting

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

Meet your guide at Siena railway station for a gentle countryside walk along the Via Francigena. Guides such as Keko, Giovanni, Francesco, and Alessia explain local history, plants, and winemaking as you walk toward Monteriggioni. Finish with a tutored tasting of local wines, free time in the medieval village, and included transport back to Siena.

“Giovanni our guide for the walk was friendly, helpful and extremely knowledgeable about the flora and fauna as we walked to Monteriggioni. Highly recommended.”

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5.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 and winemaking before five wine tastings paired with seasonal Tuscan food. Plan on taking a taxi from central Siena.

“We absolutely loved our experience. Gianluigi was very well informed, explicative and such a pleasant speaker, we could listen to him talking about wine for hours. The winery is beautiful, we tasted several wines together with delicious food. We are very glad we chose this activity during our stay in Siena.”

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6.winery tour, wine tasting and lunch

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

Walk through Chianti vineyards to the 1100s church of San Giorgio a Lapi, see frescoes by Nasini, tour the cellar, then enjoy a wine-paired Tuscan lunch on a panoramic terrace. Guides may include Jesse, Gabriele, or Giuseppe. The small group is limited to 10 people.

“Beautiful setting and excellent tour. Food and wine pairings were really good and no hard sell at the end.”

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7.Tour and Wine Tasting in a Tuscan Private Castle

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

At Castello Poggiarello near Siena, your guide, often Elena or Sveba, leads you through the castle grounds, Renaissance gardens, 16th-century chapel, and organic winery. The two-hour visit ends with a relaxed tasting of four or five wines, water, and a snack. Expect a personal look at Tuscan wine making, including unexpected international grape varieties.

“Fantastic tour, very insightful with superb wines! Massive thanks to Elena for the great tour!”

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