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Top Picks for Montalcino Experiences

Q: How many Experiences are available in Montalcino on Trip.com?

Trip.com offers 131 Experiences in Montalcino

Q: What are the best Experiences in Montalcino?

Best Winery with Restaurant and wine tasting from Florence San Gimignano Truffle Hunt & Truffle Cooking Class San Gimignano Romantic Dinner in the Vineyards

Q: What are the top-rated Experiences in Montalcino?

San Gimignano Truffle Hunt & Truffle Cooking Class Best Winery with Restaurant and wine tasting from Florence Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

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Discover 131 Experiences in Montalcino on Trip.com, updated September 30, 2025, with experiences lasting from 1 to 9 hours. Find the perfect adventure for your day!

From SGD 15.13 per person, with an average total of SGD 108.32. Choose the option that suits your plan.

With 488 verified reviews, Experiences Montalcino boast an average rating of 4.7.

This week's most popular Experiences: "Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena", with 347 reviews and a 4.9 rating.

Now on Trip.com: "San Gimignano Truffle Hunt & Truffle Cooking Class", a 3-hour adventure in Montalcino!

The next available day tour departs on October 1, 2025. Book now to secure your spot!

Montalcino Experiences usually take about 3 hours — perfect for a relaxed, immersive experience!

83% of Montalcino Experiences now offer English-speaking guides

September is the perfect time to visit Montalcino! Choose from Experiences available day tours, including seasonal favorites like Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena.

Your trip, worry-free! All day tours are run by licensed suppliers with verified reviews, and many include free cancellation before departure.

Search attractions or local attractions & tours

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Experiences

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131 Results for Montalcino Experiences

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Recommended

Best Winery with Restaurant and wine tasting from Florence

Duration: 90 mins

English

4.9/5

Excellent· 30 reviews

FromSGD 77.02

San Gimignano Truffle Hunt & Truffle Cooking Class

Duration: 3 hrs

English

5.0/5

Excellent· 8 reviews

FromSGD 484.28

San Gimignano Romantic Dinner in the Vineyards

Duration: 150 mins

English

4.3/5

Good· 26 reviews

FromSGD 192.54

Maremma: Sangiovese Wine Tasting

Duration: 2 hrs

English

FromSGD 22.69

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

Duration: 9 hrs

English

4.9/5

Excellent· 347 reviews

FromSGD 277.25

Montalcino: Brunello Wine Tasting Experience

Duration: 90 mins

English

4.6/5

Satisfactory· 40 reviews

FromSGD 50.07

Visit Best Wineries in Tuscany - Wine Tasting & Tour

Duration: 2 hrs

English

4.7/5

Great· 37 reviews

FromSGD 60.07

Corte Pavone Winery Estate: Picnic with Wine & Food + Vineyard Guided Tour

Duration: 90 mins

English

FromSGD 75.63

Corte Pavone Winery Estate: Montalcino Wine Tasting

Duration: 45 mins

English

FromSGD 45.38

Wine Tasting Small Group Tour with Lunch in Brunello

󱩳The Brunello wineries you will tour

Duration: 540 mins

English

FromSGD 272.25

Corte Pavone Winery: Local Wine Tasting With Gourmet Appetizers

Duration: 90 mins

English

FromSGD 105.88

Montalcino: Vineyard Guided Tour + Wine Tasting in the Castle

Duration: 2 hrs

English

FromSGD 89.09

Tuscany: Chianti Tour + Medici Villa Wine Tasting

Duration: 90 mins

English

FromSGD 74.12

Corte Pavone Winery Estate: Montalcino Wine Tasting + Gourmet Bites

Duration: 145 mins

English

FromSGD 52.94

Corte Pavone Winery Estate: Backstage Brunello Tour + Gourmet Tasting

Duration: 150 mins

English

FromSGD 196.62

Corte Pavone Winery Estate: Guided Winery Tour with Montalcino Wine Tasting

English

FromSGD 15.13

Montalcino: Vineyard Tour + Wine Tasting

Duration: 90 mins

English

FromSGD 49.16

Arezzo: Wine Tasting in Val di Chiana

Duration: 2 hrs

English

FromSGD 60.35

Montepulciano: Vineyard Guided Tour + Wine Tasting

Duration: 1 hr

English

FromSGD 52.79

Picnic With a Bottle of Wine in Montalcino With Optional Wine Tour

󱩳Enjoy a private picnic in the vineyards with homemade organic Tuscan specialities

Duration: 150 mins

English

FromSGD 37.82

Montalcino: Vineyard Picnic with Rosso di Montalcino Wine

󱩳A bottle of Brunello or Rosso di Montalcino

Duration: 2 hrs

Italian

FromSGD 74.12

Montalcino: Castle and Vineyards Tour with Tasting

󱩳Marvel at the architecture of an incredible medieval castle

Duration: 1 hr

Italian

FromSGD 52.94

Montalcino: Guided Winery Tour & Gourmet Food Tasting

󱩳Experience the scents and flavors of 6 wines from Montalcino

Duration: 2.5 hrs

Italian

FromSGD 121.00

Montalcino: Vineyard Picnic with a Bottle of Wine

󱩳Enjoy a private picnic in the vineyards with homemade organic Tuscan speciality

Duration: 1.5–2.5 hrs

German

FromSGD 60.50

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Reviews/Trip Moments

★

Reviews: Best Winery with Restaurant and wine tasting from Florence

Guest User2025-06-24

I cannot speak highly enough about Torciano Winery. The wine, the food, the staff and even the owner Pieriluigi was 100%. If you are within a couple hour drive, it is well worth it!!!!

★

Reviews: San Gimignano Truffle Hunt & Truffle Cooking Class

Guest User2025-06-08

Started the day with Alessandro and Spillo (the world famous truffle hunting dog!). Learned all about how truffles grow and how the dogs are trained to find them. Then off we went to follow Spillo as he raced through the woods and found multiple truffles. A fascinating experience….highly recommend! After the hunting was over, we returned to the main building and were greeted by Chef Dante. What a joy! He was so enthusiastic and knowledgeable. We chatted and laughed during the whole time we were learning classic Italian cooking methods. He taught us knife skills, showed us how to deglaze a pan, and many other techniques…but mostly how to have fun with cooking and not be afraid to try new things. To be perfectly honest, I had never had a truffle before today and I wasn’t looking forward to trying them. Was I wrong! Using the truffles we had found earlier, we made dishes that infused them in each one. First, we made tiramisu with ladyfingers quickly dipped in a sweet wine and truffles included in the layering process. (Sounds unusual but was really delicious!). Next, we made a sauce with tomatoes, zucchini, and sausage and pork tenderloin with a natural forming gravy. Finally, the pasta! I still can’t believe that I made fresh pasta! And again, every dish had some truffles added to it. Everything was so fresh and delicious! Again, I can’t say enough about how much we enjoyed working with Dante and you can’t go wrong by having him as your chef! Once we finished the cooking class, we cleaned up and were shown to a dining area to eat the dishes we made and taste many wines. We were quite impressed with our cooking skills (LOL) and thoroughly enjoyed each bite. Thank you for a wonderful experience!!!!

★

Reviews: San Gimignano Romantic Dinner in the Vineyards

Guest User2025-08-11

I found the estate online almost by chance for a mission and a once-in-a-lifetime moment: a marriage proposal. Although we spoke via email and phone, I wasn't familiar with the venue (my fault), so something unexpected could have happened. However, Barbara, first and foremost, and then Lorenzo, who accompanied us during the tasting with Chef Tony, accompanied by violinist Ivan, prepared everything to perfection, making the result incredible. A total of 10 for everything and everyone, a dream location.

★

Reviews: Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Guest User2024-10-01

Marco was our guide and he was excellent. 5/5 for him. First vineyard explained all the regulations around the brunello di montalcino wines as well as tasting with some bruschetta, in a lovely setting. The second stop was for lunch which was fantastic, cooked by the owners wife. There were further wine tastings with lunch, however there was no look around their winery. There was a very short stop (25 minutes) to briefly look around Montalcino then a stop at the third vineyard. This tour showed the winery then some small tastings. There is sales pitch, understandably, at each location and we did buy 6 bottles overall, ranging from 68 to 120 euros. It was lovely to be on such a small and intimate tour and meet lovely people as part of it. However I would suggest reducing to two vineyards and more time to explore Montalcino.

★

Reviews: Montalcino: Brunello Wine Tasting Experience

Guest User2025-09-10

Very informative and we were able to see the grapes being harvested and put through machine and tested for sugar content. Very cool. Building is an Old fortress

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