5 Siena Vineyard Tours Worldwide to Book This Year

1.A Brunello Cooking Class with Vineyards View Winery

★★★★★★★★★★5.0 · 221 reviews · 4 hours (approx.) · from $313Our pick

At Castello Tricerchi near Montalcino, a chef such as Alexandra, Gaia, or Jacomo guides you through fresh pasta and Tuscan dessert in a small group of up to 10. You’ll tour the castle and cellar, then eat your handmade meal on a terrace above the vineyards with Rosso and Brunello pairings.

“Great tour of winery and cooking class. Very relaxing and memorable! They have a wine tasting while you eat the food that you helped prepare.”

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2.From Siena/Chianti: Dinner & Drinks in the Chianti Vineyards

★★★★★★★★★★4.0 · 95 reviews · from $123

From Siena, ride by air-conditioned minivan to a Chianti farm for a sunset aperitivo, winery visit, chapel stop, and candle-lit four-course dinner. Expect roast meats, grilled vegetables, dessert, wine, and water. English, Italian, and Spanish guides lead the evening, with vegetarian meals available on request.

“The tour was very well organised and our guide was excellent.”

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3.Montalcino Castle and Vineyards tour with tasting

★★★★★★★★★★4.0 · 35 reviews · 1 hour (approx.) · from $46Best value

At Castello Tricerchi, you’ll explore a 15th-century estate, its courtyards, vineyard setting, medieval cellars, chapel, and historic rooms. An English-speaking guide such as Alice or Alessandro explains the castle and winemaking before you taste three red wines with water and breadsticks. The group is capped at 15.

“Interesting castle history although tour was short due to pouring rain. Wine tasting was great. The castle dog Nana was cute and got a lot of attention off everyone.”

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4.Small group Chianti Classico & Brunello wine region from Siena

★★★★★★★★★★5.0 · 31 reviews · 5 hours 30 minutes (approx.) · from $198

Leave Siena at 2 pm for a small-group afternoon through Chianti Classico and Montalcino. With a maximum of six people, you visit a family-run organic winery, taste Chianti with pecorino, cured meats, olive oil, and balsamic vinegar, then see Montalcino or choose a second Brunello tasting. Guides such as Morad and Stephanie add local detail.

“Our driver, Murad, was exceptionally friendly and informative - he was able to share videos of Palio di Sienna during the drive. Highly recommend!!”

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5.Sunset Summer Dinner Among the Vines – Small Group from Siena

★★★★★★★★★★3.5 · 30 reviews · 5 hours (approx.) · from $130

Leave Siena at 6 pm for Monteriggioni and a Chianti estate. You’ll tour the winery, taste wines and balsamics, then eat a generous barbecue dinner among the vines at sunset. The experience lasts about five hours and uses a small group, though pickup changes and communication can be unreliable.

“What a wonderful way to experience a boutique winery! The dinner courses were delicious as was the wine (and olive oil and balsamic offerings) We ordered a variety of wines as the price was great and so were the shipping costs, and it arrived home shortly after we did. Our driver/host was so fun and gracious and we loved visiting the walled castle town of Monteriggioni prior to our arrival to the winery. Our tour from Siena joined up with their other tour from Florence so it was a lively evening with fun people.”

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