
Montalcino: Guided Winery Tour with Tuscan Wine & Cheese Tasting
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September 2026
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Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
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Quick answer
Is Montalcino: Guided Winery Tour with Tuscan Wine & Cheese Tasting worth booking?
Montalcino: Guided Winery Tour with Tuscan Wine & Cheese Tasting is a 2-hour experience in Siena, Italy, from $40 per person. It scores 56 out of 100 on the Outty Ranking, which we label “Worth a Look”. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 56 / 100
- Rating
- Not yet rated
- Duration
- 2 hours
- From
- $40 per person
Experience the magic of Montalcino inside a medieval castle. Explore its historic cellars and enjoy a guided tasting of three exquisite wines perfectly paired with local cheeses. Book now and immerse yourself in true Tus
What you get
- Alcoholic beverages
- Food tasting
- Food & Drinks
About this experience
Experience the magic of Montalcino inside a medieval castle. Explore its historic cellars and enjoy a guided tasting of three exquisite wines perfectly paired with local cheeses. Book now and immerse yourself in true Tuscan excellence! This exclusive two-hour journey takes you to the very heart of Brunello di Montalcino production, in a setting filled with aristocratic charm and authentic rural heritage. Your visit begins with a warm welcome and an introduction to the family who has preserved this extraordinary estate for generations. The highlight of the experience is the guided tasting. This is not just about drinking—it’s about discovering. Helped by expert professionals, you will taste three estate-produced wines, including the renowned Brunello di Montalcino. What truly makes this tasting special is the art of pairing: each wine is served with a curated selection of local cheeses and handmade breadsticks.
What's included
Included
- Alcoholic beverages
- Food tasting
- Food & Drinks
Not included
- Gratuities (optional)
- Pick-up/Drop-off hotel
- Extras
Where it starts and ends
Meeting point
Siena
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
Returns to the starting point
Options you can book
Tasting in Italiano
English Tasting
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, it
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- Hidden Experiences
Know before you go
- Public transportation options are available nearby
- Not recommended for pregnant travelers
- Suitable for all physical fitness levels
Photos






Good to know
- Duration
- 2 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- 18+
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 0
- Verdict
- Worth a Look
Why this scores 56
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Montalcino: Guided Winery Tour with Tuscan Wine & Cheese Tasting: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Siena.
How much does Montalcino: Guided Winery Tour with Tuscan Wine & Cheese Tasting cost?
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Prices start at $40 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Siena usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Montalcino: Guided Winery Tour with Tuscan Wine & Cheese Tasting take?
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Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Siena is not rushed.
Is Montalcino: Guided Winery Tour with Tuscan Wine & Cheese Tasting worth it?
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It holds an Outty Ranking of 56 out of 100, which we label "Worth a Look". That score blends traveler sentiment (0/5 across 0 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Siena, and how flexible the cancellation terms are.
Can I cancel or reschedule Montalcino: Guided Winery Tour with Tuscan Wine & Cheese Tasting?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Montalcino: Guided Winery Tour with Tuscan Wine & Cheese Tasting suitable for kids and families?
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The operator sets a minimum age of 18. Older children generally do well here, and families should factor in the 2-hour running time when deciding.
How far in advance should I book Montalcino: Guided Winery Tour with Tuscan Wine & Cheese Tasting?
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Around 0 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Siena can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Siena and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.
Where does Montalcino: Guided Winery Tour with Tuscan Wine & Cheese Tasting start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Siena within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Siena?
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On Outty we rank every Siena experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena, Skip the Line: Siena Duomo and City Walking Tour, Siena: A Wine Tour and Tasting Experience. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Siena?
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Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Siena?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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