9 Siena Drinks Tours Worth Booking

1.San Gimignano, Siena, and Chianti Wine Tour

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

Leave Florence for Siena, a Chianti estate, and San Gimignano on a nine-hour guided tour. Expect air-conditioned transport, free time in both medieval towns, five wine tastings, olive oils, balsamic vinegar, and Tuscan dishes such as truffle lasagna and ribollita. Guides including Marco, Lyla, Marta, and Enrieta have earned particular praise for their energy and organization.

“Great trip, Martha was an excellent guide and made the entire trip fun. Definitely recommend this”

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2.Chianti and Castles Tour with Wine Tastings

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

Spend five hours touring Chianti from Siena in a climate-controlled minivan with up to eight people. Visit Castellina in Chianti, Monteriggioni, scenic viewpoints, and two wineries, often including Poggio ai Laghi and Lornano. Guides such as Fabio, Daniel, and Tsvetelin are praised for clear local insight, while tastings pair Chianti wines with snacks, olive oil, and balsamic.

“Thanks to our friendly and informative guide Tsvetelin we had a lovely relaxed day. Would recommend this tour to visit both the villages and for the wine tasting.”

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3.Total Immersion Wine Tour in Chianti

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

At Fattoria di Montemaggio, guide Francesco or Ilaria leads you from a 600-meter rooftop view to the vineyard, cellar, and tasting room. Learn about organic farming, Chianti Classico, wine service, and grappa, then sample five estate products with cheese, salami, bread, and olive oil. Bring a car and follow the road directions closely.

“Franceso was great very passionate about the boutique vineyard & explained lots about the history & the area. Wines were delicious & purchases were made to enjoy during the rest of our holiday. Would highly recommend going!”

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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 with an English-speaking guide such as Marco, Georgia, Paolo, or Giulia. Visit three Brunello wineries, meet winemakers, taste several wines, enjoy a family-style Tuscan lunch, and stop in Montalcino and at Sant’Antimo Abbey. The day lasts nine hours and suits wine lovers who want scenery, food, and local context in one trip.

“We had the best time on this tour. Our tour guide Marco was friendly and informative. We went to three small brunello wineries that were all special in their own ways. My favorite part was the homemade lunch at Cava D’Onice. Food was delicious and you can tell the winemaker really enjoy what he does. Can not recommend this tour enough!”

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5.Tuscany Hills Wine Tour

★★★★★★★★★★4.1 · 323 reviews · from $146

Join a full-day trip from Siena to Monteriggioni, Pienza, and Montepulciano. Taste Chianti and Nobile di Montepulciano with local snacks, enjoy free time in two hill towns, and travel by air-conditioned bus or minivan with a multilingual guide. Guides such as Marta, Vincenzo, Luciano, Lizzia, and Alberto have led past departures.

“The trip was very informative and enjoyable. Our driver Vincenzo was very knowledgeable and gave us historical and geographical information. We had enough time at the 2 wineries to take a tour and do tastings. Additionally we had enough time to eat and browse shops at the 2 towns we visited. Vincenzo was a great host and we really enjoyed our day.”

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6.Educational Wine Tour & Tasting

★★★★★★★★★★5.0 · 203 reviews · 3 hours · from $100Top rated

At Azienda Agricola La Lastra, 2 km from Siena, you’ll follow organic grapes from vine to bottle with a guide such as Maya, Christian, or Renato. Expect a three-hour visit to the vineyards and cellar, a sensory tasting of four local wines, and a generous light lunch with fresh Tuscan food. Vegetarian, vegan, and gluten-free meals can be arranged.

“This was the best winery tour we had. Maya was great explaining everything to us and the wine and lunch were amazing”

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7.Organic Winery Tour and Wine Tasting

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

Spend 2.5 hours at Azienda Agricola La Lastra, about 2 kilometers from Siena, with guides such as Maia, Mya, or Gianluigi. Walk the vineyards, learn organic grape growing and cellar work, then taste five wines with seasonal Tuscan food, including produce from the estate garden.

“Great experience with a very knowledgeable guide and tasty vine with delicious food from the local garden. Couldn’t be better!”

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

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

Leave Siena at 6 PM for a five-hour evening in Chianti. Tour a farmhouse winery, taste local wines, visit a historic chapel, then sit down to a four-course dinner with roast meats, grilled vegetables, dessert, wine, and water. English, Italian, and Spanish guides lead the outing, with hosts such as Marco, Valeska, and John appearing on different departures.

“We had a great night in the vineyards and met such nice people from around the world. Stunning view from the terrace and wonderful sit down dinner with great food and lots of wine. We were able to taste balsamic wine as well. Everyone were friends by the end of the night!”

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9.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, walking through Chianti vineyards to the medieval Church of San Giorgio, then touring the cellars before a wine-paired Tuscan lunch. Guides such as Jesse, Gabriele, and Giuseppe lead small groups of up to 10 in English or Italian.

“Jesse, our guide, provided a very interesting and informative tour and tasting. We lucked out and got a beautiful, warm, sunny day to wander through the vineyard. Lunch outside with an amazing view and different wine for each course made our visit perfect. Prior to our visit, I contacted the vineyard several times with questions. They replied quickly and were always willing to assist.”

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