15 Brunello di Montalcino Wine Tours to Build a Day Around

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

★★★★★★★★★★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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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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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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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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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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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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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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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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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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10.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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11.Chianti, Montalcino & Montepulciano – Minivan

★★★★★★★★★★4.6 · 9 reviews · from $328

10-hour Tuscan wine loop from Florence with Chianti and Montalcino tastings, a classic lunch, and time in Montepulciano.

“Booked tour thinking we were visiting town of Montalcino. We only had 10 minutes there it wasn’t worth the stop. The wine tasting a Montepulciano was in a store not a winery.The driver was nice but not a tour guide. Too expensive for what was offered.”

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12.Montalcino, Montepulciano & Val d Orcia with lunch

★★★★★★★★★★4.9 · 7 reviews · 10 hours · from $228

10-hour small-group Tuscan day trip: Montalcino Brunello tasting with lunch, Val d'Orcia UNESCO views, and free time in Montepulciano.

“Tudo incrível. Quem tiver alguma dúvida sobre este passeio, podem agendar. Vimos os melhores lugares da Toscana com a indicação do nosso guia incrível. Vale a pena o valor pago. Nossa opção foi a com almoço incluso. Tudo perfeito. Visitamos Montalcino, Montepulciano e região da Val D'Orcia. Tivemos a melhor experiência da Toscana.”

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13.Hot Air Balloon, Pienza, Montalcino, Val D’orcia

★★★★★★★★★★5.0 · 7 reviews · from $396

VIP hot air balloon ride over Val d'Orcia from Pienza and Montalcino, with champagne toast and local breakfast, guided by the wind.

“Super well organized and professional from booking, having to change date due to poor weather organizing a pick up and a magical flight over the Chianti Region. Breakfast was great too. Thank you to the entire team for a wonderful experience”

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14.San Gimignano, Chianti, and Montalcino Day Trip

★★★★★★★★★★4.5 · 6 reviews · from $158

Tuscany day trip from Siena to San Gimignano, Chianti tastings, Val d'Orcia, and Brunello in Montalcino, with expert guide.

“Winery tour and information sessions were great. Free time in San Gimignano and Montalcino was amazing, more time in both would’ve been nice. The wines were good, especially in Montalcino, and the bruschetta and cheeses were a nice touch. The meeting point was not great. We were given a spot to meet at the train station but the van picked up in a different area. If I would’nt have called the tour operator they would’ve left us behind. They left another person behind who had to find their own way to San Gimignano to meet up with the group for the rest of the tour. The tour description said we’d…”

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15.Wine Tasting with Tuscan Cold Cuts and Cheese

★★★★★★★★★★4.8 · 5 reviews · from $44Best value

Taste Brunello and Rosso di Montalcino with Tuscan cured meats and cheese, plus a vineyard walk and wine from the barrel.

“The wine was great! The visit, tasting was also great. Staff really knowledgeable and pleasant. 10/10”

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