11 Wine Tastings in Siena Worth Booking

1.San Gimignano, Siena, and Chianti Wine Tour

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

Explore Siena, Chianti, and San Gimignano from Florence with wine tasting, Tuscan lunch, medieval towns, and free time.

“Marco our tour guide was amazing! He was very knowledgeable and explained everything clearly. He also made sure to talk and connect with many of the people on the tour individually, so it felt very personalized! The tour itself was also incredible - being able to see all the beautiful areas that I did in one day? 10/10”

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2.Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

★★★★★★★★★★5.0 · 952 reviews · 9 hours (approx.) · from $217Top rated

Taste Brunello at three family wineries, enjoy a homemade Tuscan lunch, and visit Montalcino and Sant’Antimo from Siena.

“Giorgia was an excellent guide to the best wine we experienced in Italy! She was full of interesting facts and history of the region. It made the experience lively and educational. She made sure all in the tour were included in conversation and all of us had a great time! Our favorite winery was Fattoria del Pino with winemaker Jessica!!! All the wineries were excellent including our lunch by Gianni Bernazzi. Thank you for an amazing experience! Grazie!”

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3.Chianti and Castles Tour with Wine Tastings

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

Review of Siena’s five-hour Chianti tour, with two wineries, Castellina, Monteriggioni, scenic stops, wine, snacks, and practical tips.

“We had the most wonderful afternoon on this tour. It’s a great tour if ‘tours’ aren’t really your thing. It’s more guided transport to each area (beautiful little villages, two wineries and the castle) with time by yourself to just wander, eat, have wine tastings and experience the beauty of each area. The guides are informative, personable and genuine. We made friends with the other couples in our group and ended up all meeting for dinner later that night. For the cost of the tour I absolutely recommend it. It’s exceptional. 😊”

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4.Total Immersion Wine Tour in Chianti

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

Explore Chianti Classico wines, organic farming, cellar craft, and Tuscan views at family-run Fattoria di Montemaggio.

“the guide was very freindly and he really created an experience we will not forget.”

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5.Brunello di Montalcino Guided Wine Tour W/ Lunch

★★★★★★★★★★4.9 · 357 reviews · from $203

Spend nine hours tasting Brunello at three Montalcino wineries, enjoying a Tuscan lunch, and visiting Montalcino and Sant’Antimo Abbey.

“Paulo is an excellent guide to Italian wine, history and culture. Spectacular walk, excellent wines mainly in Bellaria and Terre Nere which are small and familiar.”

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6.A Wine Tour and Tasting Experience

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

Tour Siena’s organic vineyards, learn winemaking from grape to bottle, taste four wines, and enjoy a seasonal Tuscan lunch at La Lastra.

“Very disappointed in this company and Viator. We had booked this wine tour and had severe weather notice. I alerted Viator hours in advance of the event only to have them say there would be no refund! Be very careful if you are booking any outdoor events with this company and tour as you won't get a refund of your money and it was expensive!! I'm so disappointed and frustrated at this experience.”

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7.Tuscany Hills Wine Tour

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

Review of Siena’s Tuscany Hills Wine Tour, with Chianti and Nobile tastings, Pienza, Montepulciano, transport, timing, and practical tips.

“I had great time on this tour, met some amazing people and get to see Montelcino, Pienza and Montepulciano which are all amazing little villages. both of the wineries we visited were amazing in their own way, great wine to taste/purchase. the tour guide was amazing, so overall I received more than I paid for, amazing day out.”

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8.Visit Best Wineries in Tuscany – Wine Tasting & Tour

★★★★★★★★★★4.5 · 263 reviews · 2 hours (approx.) · from $47

Taste Tuscan wines, olive oils, cheeses, and salami at Tenuta Torciano near San Gimignano, with a winery visit and optional meal.

“Absolutely sublime evening tasting a variety of wines with superb complimenting appetisers. We felt really looked after by Latisha who explained the different wines, of which tasters were plentiful! Even our daughter who couldn’t drink the wines was able to learn how to correctly hold the glass, and pick up on different aromas…they even cooked some spaghetti for her! We felt under no obligation to buy and as a result, we will absolutely look for the Tenuta brand when we are next buying wine. Thank you!”

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9.Educational Wine Tour & Tasting

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

Learn organic winemaking near Siena with vineyard and cellar visits, four wines, a generous Tuscan lunch, and beautiful countryside views.

“Amazing experience. You learn a lot while drinking and eating delicious wines/meals. Highly recommend !!!”

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10.San Gimignano, Chianti & Montalcino Small-Group Tour

★★★★★★★★★★4.6 · 195 reviews · from $158

Review this 11-hour Siena tour through San Gimignano, Chianti, Montalcino, and Val d'Orcia, with two tastings and a small-group van.

“Fabulous driver/guide who could speak multiple languages really well and had deep local knowledge (including winemaking processes), lovely comfortable vehicle to travel in, stunning scenery, the right amount of time in each town and wine tasting with genuine local authentic quality wine makers (plus lovely food). We highly recommend this trip!”

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11.San Gimignano: Lunch or Dinner at a Winery with Wine Tasting

★★★★★★★★★★4.7 · 177 reviews · 1.5 - 2 hours · from $65

Enjoy a Tuscan meal, guided wine and olive oil tasting, and Chianti views at Tenuta Torciano near San Gimignano for $65.

“Outstanding experience with amazing wines and food in a superb setting. Excellent value for money.”

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