15 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.Siena, San Gimignano and Chianti Small Group Tour

★★★★★★★★★★4.9 · 433 reviews · 9 hours · from $175

Review of a 9-hour Florence tour to Siena, San Gimignano and Chianti, with guided sightseeing, Tuscan lunch, wine tasting and practical tips.

“Davide was an excellent tour guide. He was knowledgable and gave us a wealth of information, while we were on route to prepare us. At the same time, he gave us time to rest and process the information. This tour was well worth the money. It was clear that Davide enjoys guiding tourists and wants to give them their money’s worth. Jean Lucas was an experienced driver.”

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5.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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6.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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7.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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8.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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9.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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10.A Brunello Cooking Class with Vineyards View Winery

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

Review of a Brunello cooking class near Montalcino, with handmade pasta, castle history, cellar tour, wine pairings, and vineyard views.

“This was an absolutely amazing experience. We are traveling in a group of six married couples celebrating our 40th birthdays. The castle is a quiet dream originally constructed in the 1200s a top a hill overlooking the Tuscan hills and vineyard. You can see Montalcino a few miles away on its hilltop as well. The cooking class is in a small rustic building with gorgeous windows overlooking the winery. A mom and daughter team led our cooking class, starting with tiramasu, beef and pasta, while being served Persecco. We had lunch outside on a terrace where we were served their delicious wine. This has been the highlight of our two…”

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11.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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12.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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13.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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14.Hidden Castles & Chianti Wine Experience– Small Group

★★★★★★★★★★4.5 · 172 reviews · 5 hours (approx.) · from $59

Explore Chianti from Siena with two winery tastings, Tuscan villages, castle views, local snacks, and an easy small-group minivan ride.

“I had a deeply disappointing experience with this wine tour. After booking and receiving confirmation, the guide never showed up on the scheduled day. We waited for over an hour, tried reaching out to the company multiple times, but received no response. We especially traveled by train to Siena for this tour, and they never showed up, which is very unprofessional. It completely ruined our plans and wasted our time. If you value your time and money, I’d recommend finding a more reliable tour operator. This experience was unacceptable, and I hope they improve their communication and accountability in the future.”

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

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

Review of a Tuscany day trip from Florence to San Gimignano, Siena, Monteriggioni, and Chianti, with lunch and wine tasting.

“Overall: Great destinations, great guide, poor lunch, too many people. Great tour guide, very friendly. Fantastic locations. Too many people for it to be personal at all. It’s a full double-decker Coach bus completely filled with people. If you get stuck sitting in the back of the bus, you have to wait for everyone else to get off first which wastes time at each location. Felt like a hierarchy of seating arrangement. Winery lunch was mediocre. Winery was not spectacular. They turn over hundreds of people a day and the food was basic. Lots of yelling to explain each wine.”

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