4 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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