15 Brunello di Montalcino Wine Tours to Build a Day Around

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena - Stop 1: Vineyard Walk, Cellars, and the First Round of Brunello

★★★★★★★★★★5.0 · 952 reviews · 9 hours (approx.) · from $217Our pick

Small-group Brunello day trip from Siena with three tastings, family lunch, and Sant'Antimo abbey visits. English tour, 9 hours.

“My husband and I recently spent a full-day wine tour around Siena that exceeded every expectation. We visited three distinct vineyards, enjoyed guided tastings at each, and savored a chef-prepared lunch at the second estate. The scenery, the wines, and the overall pacing of the day were wonderful — but what truly made the experience unforgettable was our guide, Juliana. Juliana’s knowledge of the region is remarkable. She explained the terroir, soil types, and microclimates with clarity and enthusiasm, tying each detail directly to the character of the wines we tasted. Her history of the local grape varieties, and the stories about how winemaking traditions evolved in the area, were…”

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Val d’Orcia Brunello Wine Tour with Montalcino and Montepulciano

2.Val d’Orcia Brunello Wine Tour with Montalcino and Montepulciano

★★★★★★★★★★4.5 · 359 reviews · 10 hours 30 minutes (approx.) · from $277

Florence to Val d'Orcia: Brunello and Nobile tastings in Montalcino and Montepulciano, Pienza lunch, castle stops and views.

“Great day in Tuscany. I want to say thank you to Simona and the wineries for making our experience wonderful. Simona went above and beyond to help make it a great day. Thank you Simona. Ci rivediamo presto speriamo!”

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From Siena: Brunello di Montalcino Guided Wine Tour W/ Lunch

3.Brunello di Montalcino Guided Wine Tour W/ Lunch

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

Small-group Brunello tour from Siena with 3 winery visits, tastings and lunch, Montalcino town time, and Sant'Antimo.

“Our guide Marco was so friendly and kind. He told us a lots of useful information of Montalcino wine. And sight seeing was also wonderful”

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Montalcino: Brunello Wine Tasting & Lunch in a Tuscan Castle

4.Brunello Wine Tasting & Lunch in a Tuscan Castle

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

Exclusive Brunello tasting and Tuscan lunch in Castello Tricerchi, Montalcino. Walk the vines, taste 3 wines, then eat well for $69.

“Our guide, Alice, was extraordinary. She was very knowledgeable, friendly, and was genuinely interested in getting to know us. The grounds and the castle were beautiful and the lunch/wine tasting was superb. We were never rushed and enjoyed every minute of the experience.”

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Florence: Valdorcia Wine, Brunello Montalcino, Montepulciano

5.Valdorcia Wine, Brunello Montalcino, Montepulciano

★★★★★★★★★★4.8 · 238 reviews · 10.5 hours · from $265

From Florence, tour Val d'Orcia with Brunello tasting in Montalcino, lunch in Pienza, and underground Vino Nobile in Montepulciano.

“What a wonderful day! Mike, our driver, was so nice and provided some great history along the drive. We never felt rushed by him. The wineries and towns were spectacular. I would absolutely recommend this tour to others!”

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Florence: Orcia Valley, Montalcino, Pienza with Lunch & Wine

6.Orcia Valley, Montalcino, Pienza with Lunch & Wine

★★★★★★★★★★4.7 · 225 reviews · 12 hours · from $123

Full-day Val d’Orcia trip from Florence to Pienza, Montalcino, the Temple of Brunello, and Sant’Antimo, with lunch and 3 wine tastings.

“Our guide Julia and our driver, had the best sense of humor and most knowledgeable. We traveled through the beautiful Tuscany hills comfortably in a AC coach bus. We loved all the small towns, the history Nd the ample time we had to walk around. The best part by far was the dinner and wine tasting! Molto bene😘🤌”

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A Brunello Cooking Class with Vineyards View Winery

7.A Brunello Cooking Class with Vineyards View Winery

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

Small-group Brunello cooking class in Montalcino with Castello Tricerchi winery and cellar tour, plus terrace lunch with wine pairings.

“From our tour of the winery to our cooking….SO great. We learned about the winery, cooking techniques……then put the food and wine together for a really great experience!”

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Siena: San Gimignano, Chianti & Montalcino Small-Group Tour

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

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

Small-group day trip from Siena to San Gimignano towers, Chianti tastings, UNESCO Val d’Orcia views, and Brunello in Montalcino.

“I think its too much for one day. I heard everyone in my group say going to Montalcino was not worth the time”

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San Gimignano, Chianti, and Montalcino Day Trip from Siena

9.San Gimignano, Chianti, and Montalcino Day Trip from Siena

★★★★★★★★★★4.5 · 150 reviews · 11 hours (approx.) · from $168

San Gimignano, Chianti, and Montalcino day trip from Siena with early hill-town time, big wine tastings, and Val d’Orcia views.

“It was a terrific experience - a great day exploring parts of Tuscany with our driver and guide Ganti and four other co-travelers. The morning stop at St. Gimignano was enjoyable though a little long because we got there early. Lunch at the winery was the highlight of the day - a fabulous private room among the barrels and bottles with our own guide Bledard who gave us a terrific wine experience with wonderful Chiantis. The food was great too. Then, we visited another winery that showcased the Rosso and Brunello Montalcinos - walked down to the underground cellar which was very cool and then tasted wines with bread and…”

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Brunello Wine Tour and Val D’Orcia Landscape

10.Brunello Wine Tour and Val D’Orcia Landscape

★★★★★★★★★★5.0 · 93 reviews · 4 hours (approx.) · from $266

Private Brunello di Montalcino wine tour from Pienza with UNESCO Val d’Orcia scenery, customizable tasting at a family winery, pickup.

“Fabrizio was the most caring and detail oriented guide that I/we have ever had. He truly customized the tour for us. We were able to take longer in areas that we wanted to. He just wanted us to make the most out of our day. Brunello wine tour was the best of all after taking all into consideration! Book this tour and you will be amazed!!!”

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Brunello and Nobile, Wine Lover Tour Montalcino and Montepulciano

11.Brunello and Nobile, Wine Lover Tour Montalcino and Montepulciano

★★★★★★★★★★5.0 · 88 reviews · 9 hours (approx.) · from $938

Private Brunello and Nobile wine day from Florence. Medieval towns, Val d’Orcia views, and tastings with an English guide.

“This was an excellent way to spend a day outside of the City and to see the beautiful wine country of Tuscany. Our private car was excellent, clean and spacious for our family of four. Our guide, Dario, was pleasant and did an excellent job taking us to two amazing locations to experience the Brunello area. He was also extremely knowledgeable about the wine and was able to answer every question we had. The small family owned winery we visited was nothing short of amazing. Their Brunello was outstanding, the tour of the family production area was nice, and the small lunch they provided was perfect. This was a must…”

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Montalcino: Vineyard Picnic with a Bottle of Wine

12.Vineyard Picnic with a Bottle of Wine

★★★★★★★★★★4.9 · 87 reviews · 1.5 - 2.5 hours · from $47

Vineyard picnic at Corte Pavone Winery in Montalcino with a wine tasting and a bottle to take home, plus homemade Tuscan specialties.

“O local é lindo, mas pagamos o piquenique para nosso grupo de 5 pessoas, onde uma não bebia nada alcoólico e pagou o mesmo preço dos demais. Além disso, nem essa pessoa e nem a criança que estavam conosco tinham nada além de água comum para beber. poderia haver, ao menos, um suco de uva, por exemplo. Outra coisa é que apesar de todos, com a exceção da criança, terem pago valor integral do passeio, só foram oferecidas 2 garrafas de vinho.”

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Olive Oil Tours and Tasting at Frantoio di Montalcino

13.Olive Oil Tours and Tasting at Frantoio di Montalcino

★★★★★★★★★★5.0 · 85 reviews · 1 hour 30 minutes (approx.) · from $60

Tour an olive mill in Montalcino, taste multiple extra virgin olive oils with bread, and shop for bottles to take home in English.

“Small but great facility, very clean, great description of the olive oil making process, no pressure to buy, food and oils were yummy, we purchased the 50 euro highest polyphenol oil for ourselves and 1 as a gift.”

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Montalcino: Brunello Wine Tasting Experience

14.Brunello Wine Tasting Experience

★★★★★★★★★★4.2 · 84 reviews · 1.5 - 2 hours · from $38Best value

Taste 3 Brunello-area wines in a medieval Montalcino castle, with a vineyard walk and local bread pairings, led by an expert sommelier.

“Alice was the best! The wine was delightful. Cannot recommend this experience enough!”

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Montalcino: Private Cellar Tour, Wine Tasting & Appetizers

15.Private Cellar Tour, Wine Tasting & Appetizers

★★★★★★★★★★4.7 · 82 reviews · 1.5 hours · from $81

Private cellar tour at Paradiso di Cacuci in Montalcino, taste 5 wines including Brunello, and enjoy Tuscan appetizers with a guide.

“A noi è capitato l'enologo della cantina come guida, preparato e simpatico. i vini sono eccellenti, luogo incantevole. tutti molto gentili e professionali. esperienza consigliatissima.”

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