
VIP Chianti, Brunello wine & Pienza with lunch From Siena
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
Select a highlighted day to see live departure times and the exact price for your group.
Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 28 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is VIP Chianti, Brunello wine & Pienza with lunch From Siena worth booking?
VIP Chianti, Brunello wine & Pienza with lunch From Siena is a 8-hour experience in Siena, Italy, from $235 per person. It scores 74 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 5/5 rating across 28 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 74 / 100
- Rating
- 5/5 (28)
- Duration
- 8 hours
- From
- $235 per person
This is a semi- private with maximum 6 people in tour so you will have all the attention you need. This tours will give you the advantages to truly enjoy the experience and not have to be in a crowded bus and follow a st
What you get
- Small group max 6 people
- Tour of 2 wineries historical cellars
- Extra virgin Olive oil tastings
- Brunello di Montalcino, Super tuscans & Chianti Classico
- Licensed tour guide
- Alcoholic beverages
About this experience
This is a semi- private with maximum 6 people in tour so you will have all the attention you need. This tours will give you the advantages to truly enjoy the experience and not have to be in a crowded bus and follow a strict schedule . We will visit 2 beautiful boutique family owned wineries in a relaxed atmosphere and meeting the locals. You will taste top rated wines like Chianti Classico & Brunello di Montalcino while enjoying beautiful views and learning all the secrets of the best wine regions in the world.
What's included
Included
- Small group max 6 people
- Tour of 2 wineries historical cellars
- Extra virgin Olive oil tastings
- Brunello di Montalcino, Super tuscans & Chianti Classico
- Licensed tour guide
- Alcoholic beverages
- Lunch
Not included
- Museums tickets
What you'll see and do
Siena
Introduction to Sienna's History by a Licensed Tour guide from a panoramic view point overlooking the city.
30 minutes here
Castellina In Chianti
Our next stop will be an amazing organic boutique winery family owned. Here you will experience the atmosphere of the Chianti region surrounded by a breathtaking view over the Tuscan hills. In addition to the wine tasting and wine historical cellars , enjoy a delicious Tuscan Lunch with products like Pecorino cheese, cold cuts and homemade pasta.
120 minutes here
Montalcino
Here you will visit a family owned boutique winery and enjoy Brunello di Montalcino with breathtaking views over the valley. You will also visit the cellars and learn all the secrets about Brunello di Montalcino wine, listed as best wine in the world 2023.
60 minutes here
Val D'Orcia
Enjoy beautiful rolling hills and the the Unesco site of Val d'orcia, where the Gladiator movie scene was filmed.
Pass by without stopping
Pienza
Last stop will be the picturesque town of Pienza and val d'Orcia with impressive landscape to admire and the “Touchstone of Renaissance Urbanism.” Considered an artistic jewel of the landscape of Val d’Orcia, Pienza is a perfect combination of architectural beauty and harmony. Pienza’s most renowned tradition is Pecorino cheese.
60 minutes here
Where it starts and ends
Meeting point
Siena
OUTSIDE PROSPERINO BISTROT. THE GUIDE WILL BE WAITING OUTSIDE ON THE TERRACE, NEXT TO THE OLIVE TREE STATUE.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
OUTSIDE PROSPERINO BISTROT. THE GUIDE WILL BE WAITING OUTSIDE ON THE TERRACE, NEXT TO THE OLIVE TREE STATUE.
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
- Fri, Sat
- Group size
- Up to 4 travelers per booking
- Operated by
- Moro Tuscany Tours
Know before you go
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Not recommended for travelers with spinal injuries
- Not recommended for pregnant travelers
- Not recommended for travelers with poor cardiovascular health
- Travelers should have at least a moderate level of physical fitness
- This tour has been upgraded for 2025 so the reviews may be different from description.
Photos






Good to know
- Duration
- 8 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- 18+
- Availability
- Bookable today
- Runs on
- Fri, Sat
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 10
- Verdict
- Strongly Recommended
Why this scores 74
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
VIP Chianti, Brunello wine & Pienza with lunch From Siena: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Siena.
How much does VIP Chianti, Brunello wine & Pienza with lunch From Siena cost?
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Prices start at $235 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 VIP Chianti, Brunello wine & Pienza with lunch From Siena take?
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Plan for about 8 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 VIP Chianti, Brunello wine & Pienza with lunch From Siena worth it?
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It holds an Outty Ranking of 74 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (5/5 across 28 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in Siena, and how flexible the cancellation terms are.
Can I cancel or reschedule VIP Chianti, Brunello wine & Pienza with lunch From Siena?
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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 VIP Chianti, Brunello wine & Pienza with lunch From Siena 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 8-hour running time when deciding.
How far in advance should I book VIP Chianti, Brunello wine & Pienza with lunch From Siena?
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Around 10 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 8-hour experience runs outdoors or after sunset.
Where does VIP Chianti, Brunello wine & Pienza with lunch From Siena 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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