Top 12 Wine Tastings in Siena

1.San Gimignano, Siena, and Chianti Wine Tour

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

Travel from Florence by air-conditioned minibus to Siena, a Chianti winery, and San Gimignano. You get guided context, free time, five wine tastings, olive oils, and a Tuscan meal. Guides such as Marco, Lyla, Marta, and Enrieta are praised for keeping the day friendly and well timed.

“Oh such a lovely day it was and our guide Lyla was very communicative and made the tour very fun. Our driver, Antonio, was also a very sweet person. She explained about the very interesting history of places and the wines too. There was intern from the company who also gave a lot of information about the last stop. Overall, it was great day, relaxed and every minute of the tour was used. The cherry on top was everybody and everything was on time. Highly recommend this tour.”

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2.Chianti and Castles Tour with Wine Tastings

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

Travel from Siena in a comfortable eight-seat minivan with an Italian, English, or Spanish-speaking guide. Visit Castellina in Chianti and Monteriggioni, pause for views and free time, then taste Chianti wines at two distinct estates such as Poggio ai Laghi and Lornano.

“Our guide was knowledgeable, kind and fun which made for a great tour for us all. The activities Chianti wine tasting and villages were with castles were amazing and all fitted into one afternoon so perfect.”

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3.Montepulciano: Wine Tasting and Cellar Tour

★★★★★★★★★★4.8 · 545 reviews · 1 hour · from $38Best value

Spend an hour beneath Montepulciano tasting Nobile di Montepulciano and other Tuscan wines. Your English or Italian guide explains the De’Ricci cellar, tufa soil, and oak aging, followed by pecorino, bruschetta, crostini, and possibly a sixth pour depending on the session.

“Amazing tour loved very bit of it. Every once in a while I order some wine from the Contucci Cellar. loved it”

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4.Total Immersion Wine Tour in Chianti

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

At Fattoria di Montemaggio, Francesco, Ilaria, or Stefano leads you from a 600-meter rooftop view through the vineyard and cellar. Learn organic winemaking, taste five estate products, and sample cheese, salami, bread, olive oil, and grappa in a small, personal setting.

“Ilaria is a great passionate guide. She made us a tour of the vineyard and the cellar with clear and lively explanation. Also mentioned some interesting information regarding organic farming. Tasting was great with some food and generous servings. Just a note : no discount on bottles vs retail price.”

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5.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 Daniele. Visit three very different Brunello wineries, taste cellar-aged wines, eat lunch at a family-run estate, and stop in Montalcino and at Sant’Antimo Abbey.

“What a great tour! We visited 3 fantastic wineries and had the pleasure of trying several selections of their wines. And Georgia was a wonderful tour guide; very insightful, knowledgeable, and accommodating. We couldn't have asked for a better day.”

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6.A Wine Tour and Tasting Experience

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

Meet at Azienda Agricola La Lastra outside Siena for a three-hour visit through organic vineyards and the wine cellar. Guides such as Maya and Maia explain grape growing, winemaking, tasting, and food pairing before four wines, olive oil, and a seasonal Tuscan lunch.

“Found this wine and food tour and loved it. Beautiful setting in the winery. We toured the vineyard and cellars. Then the wine pairing!!! So good my husband bought a case to take away and one shipped home. Loved the fact that it was organic. Our guide. (Sorry can’t remember her name!) was very knowledgeable and took great pictures of us in the vineyard. Met some lovely travelers and shared food and wine. Two thumbs up.”

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7.Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

★★★★★★★★★★4.6 · 324 reviews · 1.5 hours · from $69

Meet your English- or Italian-speaking sommelier at Castello Tricerchi, stroll through the vineyard, hear the estate’s story, and taste three Tuscan wines with local snacks. Finish with cold cuts, cheeses, handmade pasta, dessert, and coffee in a medieval castle.

“We had an engaging time listening to Allessio explain the wine making process and the history of the Tricerchia family and Castle The wine tasting and lunch at the end of the tour was a great finish Gracie!”

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8.Tuscany Hills Wine Tour

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

Travel from Siena by air-conditioned bus or minivan through Chianti and Val d’Orcia. Taste wines with local snacks at two wineries, explore Pienza and Montepulciano on your own, and hear regional stories from multilingual guides such as Marta, Vincenzo, and Luciano.

“Downside a bit of confusion at the beginning of the trip while waiting for connecting bus from Florence. Communication could have been better. Lastly at the end of the tour the bus dropped us off at night in the outskirts of the city of Siena and it was difficult to find our accommodations from that point. Would have been better to drop us off at La Lizza Bar.”

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9.Educational Wine Tour & Tasting

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

Spend three hours at Azienda Agricola La Lastra, just 2 km from Siena, with a guide such as Maia, Christian, or Renato. Walk through organic vineyards, visit the cellar, taste four local wines, and share a seasonal Tuscan lunch with food and wine pairings.

“We lucked up with nice weather and our guide was the owner. He was passionate about his vines, respecting the environment, keeping them healthy organically. He told us about the process of making his wines from the grapes grown in the two vineyards that he operated. After time in the field and viewing the operations, we sat at a beautiful large table for a light lunch and wine tasting. My husband said this was his favorite tour of our whole trip to Italy. You do have to make your own way to the winery and back just outside of Siena. So read the details and allow time to catch a…”

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10.Montalcino: Guided Winery Tour and Wine Tasting

★★★★★★★★★★4.8 · 200 reviews · 1h 45m · from $53

At Corte Pavone Winery near Montalcino, an English- or Italian-speaking guide leads you through biodynamic vineyards, grape-processing rooms, and a cross-vaulted cellar before six wines arrive in three flights. Choose a Brunello, Maremma, or full-estate tasting.

“Great tour trough the fields and great guide (man with the earring 😊). I didn’t know one could know so much about wine. The explanation was very enlightening.”

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

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

Travel from Siena in a minivan for a full day of Tuscan towns, vineyards, and views. You’ll explore San Gimignano and Montalcino, taste Chianti and Brunello, and stop for local snacks. Guides including Fabio, Vincenzo, Luca, and Michele have led this route.

“This was a fantastic 11-hour tour of Tuscany out of Siena. The scenery is so amazing and beautiful. The van (Mercedes!) picked us up & dropped us off at our hotel for door to door service. We had 6-people on the tour plus our driver/tour guide. He was very knowledgeable about every where we went. Stopped at 2-winery's where we sampled a number of wines & some cheese plates. Also stopped at a number of medieval walled towns...San Gimagnano, Montalcino, & Monteriggioni. Walking around in these towns was so amazing when you realize they were built in the 11th & 12th century. We highly recommend this tour.Read more”

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12.Montepulciano: Winery Tour and Tasting

★★★★★★★★★★4.6 · 187 reviews · 1.5 hours · from $41

Meet at Talosa Cantina Storica for a 1.5-hour visit beneath Montepulciano. A sommelier such as Luigi or Flavio guides you through old vaults, tunnels, barrels, and local wine, including Rosso and Nobile di Montepulciano, with bread, water, cheese, and cured meats.

“Better than expected! The tour isn´t that big but it was really okay!”

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