Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE
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September 2026
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Adults
Age 13 and over
Children
Age 12 and under
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Non-refundable booking. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 11 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE worth booking?
Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE is a 8-hour experience in Siena, Italy, from $200 per person. It scores 60 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 11 reviews. This booking is non-refundable, so pick your date carefully. Same-day spots are currently showing.
- Outty Ranking
- 60 / 100
- Rating
- 5/5 (11)
- Duration
- 8 hours
- From
- $200 per person
* Private, Exclusive, Customizable, door-to-door tour of Pienza, Val d'Orcia, Montalcino, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan with air conditioning and knowledgeable English spe
What you get
- Hotel pickup and drop-off
- Free Wi-Fi on board
- Round-trip private transfer
- Gas - Tolls - VAT
- Refreshments on board
About this experience
* Private, Exclusive, Customizable, door-to-door tour of Pienza, Val d'Orcia, Montalcino, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan with air conditioning and knowledgeable English speaking driver * Free Wi-Fi on board * Refreshments on board * Gas - Tolls - VAT
What's included
Included
- Hotel pickup and drop-off
- Free Wi-Fi on board
- Round-trip private transfer
- Gas - Tolls - VAT
- Refreshments on board
Not included
- Lunch
- Gratuities
What you'll see and do
Azienda Agricola Capanna di Cencioni
Family-run boutique winery for visit and wine tasting
60 minutes here · Admission included
Pienza
Explore this quaint village on a self guided tour
30 minutes here
Val D'Orcia
Panoramic drive through this UNESCO heritage site with stops for photos
Pass by without stopping
Where it starts and ends
Hotel pickup
Pickup is included for all travelers.
Before you book
- Cancellation
- All sales are final. No refund is available for cancellations.
- Languages
- pt, en, it, fr
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 8 travelers per booking
- Operated by
- We Drive You Tuscany
Know before you go
- Public transportation options are available nearby
- Infants are required to sit on an adult’s lap
- Specialized infant seats are available
- Travelers should have at least a moderate level of physical fitness
- Vegetarian option is available, please advise at time of booking if required
- A minimum of 2 people per booking is required
- A maximum of 8 people per booking
- Operates in all weather conditions, please dress appropriately
Photos
What travelers are saying
Outty’s summary of the themes that recur across 11 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
9 mentionsReviewers describe the commentary as informative rather than scripted.
Food and drink
9 mentionsThe tastings and food stops are a highlight for most reviewers.
The guide
8 mentionsTravelers single out the guide as the reason the experience works.
Good for families
4 mentionsReviewers traveling with kids report it landed well with their group.
Small groups
3 mentionsThe group size is repeatedly described as intimate rather than packed.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Traveler reviews
11 verified traveler reviews for Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE. Ratings and reviews provided by Viator and Tripadvisor.
Roberto is a fun and brilliant tour guide in Sienna. Don’t hesitate to book with We Drive You Tuscany.
My family spent two days with Roberto as our driver. I cannot say enough amazing things about him!!! We visited some of the most beautiful places of Tuscany during our two day tour. Roberto picked us up at our requested time at our hotel. We didn’t have to navigate to any meeting spots, and we loved that convenience. His tour was so informative on the area, art, history and culture. The breadth of knowledge Roberto had on Roman history and Italian art was impressive!! On our tour, we also had some rich experiences with small local wineries and a sheep farm that makes fresh cheese. Roberto took us to all the lovely towns in the Val D'orcia. The pace was perfect and we saw so much in the two days. We were not disappointed as we are with some tours, Roberto took us to see everything! He squeezed in all the important sights and many small, amazing lesser known places as well!!! We hope to come back and tour Umbria and Florence with Roberto sometime soon!
Response from the operator: Thank you for your note. We are glad that you had a good time and were well looked after by Roberto. We hope to be able to welcome you back again in the future.
via Tripadvisor
Great day of Brunello tastings
We had a fantastic experience with our driver, Roberto. Not only was he professional, he was authentic, knowledgeable, and personable. He knew the history of Tuscany and was able to give us recommendations to avoid the tourist traps. He was beloved by all the staff of all the wineries we visited. We've been on other private tours where the tour guide was just a driver, but Roberto was a true host and then some.
Response from the operator: We very happy to hear that Roberto looked after you well and you had a good day out.
via Tripadvisor
Highly recommend!
Me and my friends had an amazing time, we were a group of 3, did a private tour from Florence to Pienza, Val D'Orcia, brunello wine and pecorino cheese tasting. Everything went smoothly, from hotel pick up to drop off. Our driver Roberto, was fantastic, he is very knowledgeable and relatable. We had conversations about almost everything, from Italian history, art, culture, all the way to life experiences, which we will remember and cherish for a very long time. We also had lunch in a farmhouse in Tuscany with Elia, who was very kind, hospitable, and welcoming. He served us local cuisines and delicacies from Tuscany, which we all enjoyed. Highly recommend this tour, they have amazing people, who will make sure you and your family/friends would enjoy your trip.
via Tripadvisor
A great tour through Tuscany
Excellent experience. The driver guide Roberto was simply sensational. . He demonstrated great flexibility by adjusting the itinerary to our preferences, replacing the visit to Pienza, which we already knew, with Montepulciano, and including a stop for lunch at a great restaurant in Bagno Vignoni. A very cultured and polite professional, he brought extra quality to the tour of sensational places.
via Tripadvisor (translated)
Brunello Wine Tasting
Roberto was incredible and so knowledgeable on a variety of topics. He was funny and kept the conversation lively. He truly loves what he does and it does not go unnoticed. The wineries we went to were small production and you can tell how much passion they have for wine making. They made us feel like they were part of our family. The lunch we had was incredible and homemade. Roberto picked us up directly at our accommodation and dropped us off. I highly recommend booking with this group as they truly care about your experience in Italy. Grazie mille for a lovely experience
via Tripadvisor
Good to know
- Duration
- 8 hours
- Free cancellation
- Non-refundable
- Minimum age to book
- 10+
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $200 to $580
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 4
- Verdict
- Worth a Look
Why this scores 60
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Siena.
How much does Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE cost?
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Prices start at $200 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 Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE 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 Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE worth it?
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It holds an Outty Ranking of 60 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 11 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable food & drink in Siena, and how flexible the cancellation terms are.
Can I cancel or reschedule Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE?
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No. This experience is sold on a non-refundable basis, so only book a date you are confident about. Similar experiences in the city do offer free cancellation if flexibility matters more than price.
Is Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE suitable for kids and families?
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The operator sets a minimum age of 10. 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 Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE?
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Around 4 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 Pienza, Montalcino, Brunello Wine and Pecorino Cheese PRIVATE TOUR from FLORENCE 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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