
Private Montalcino and Pienza Tour from Siena
Traveler rating
4.0/5
Based on 3 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Montalcino and Pienza Tour from Siena worth booking?
Private Montalcino and Pienza Tour from Siena is a 6-hour experience in Siena, Italy, from $533 per person. It scores 52 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 4/5 rating across 3 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 52 / 100
- Rating
- 4/5 (3)
- Duration
- 6 hours
- From
- $533 per person
Travelling through the Val d’Orcia is an unforgettable experience. Your eyes will be dazzled by the colours and harmony of this landscape, unsurprisingly listed as a UNESCO World Heritage Site. This tour is designed to let you discover the most iconic and photographed corner of Tuscany, with its enchanted scenery and tree-lined avenues. We will explore the legendary road that stretches from Montalcino to Pienza, considered one of the most beautiful routes in Italy. Guests will enjoy one hour of free time in Montalcino to stroll, shop, or simply soak in the atmosphere, and one hour of free time in Pienza, the “ideal Renaissance city.” Here, you will also enjoy a cheese tasting in a traditional local shop, discovering the flavours of the famous Pecorino di Pienza. Pick-up and drop-off from your hotel or apartment in Siena are included.
What you get
About this experience
Travelling through the Val d’Orcia is an unforgettable experience. Your eyes will be dazzled by the colours and harmony of this landscape, unsurprisingly listed as a UNESCO World Heritage Site. This tour is designed to let you discover the most iconic and photographed corner of Tuscany, with its enchanted scenery and tree-lined avenues. We will explore the legendary road that stretches from Montalcino to Pienza, considered one of the most beautiful routes in Italy. Guests will enjoy one hour of free time in Montalcino to stroll, shop, or simply soak in the atmosphere, and one hour of free time in Pienza, the “ideal Renaissance city.” Here, you will also enjoy a cheese tasting in a traditional local shop, discovering the flavours of the famous Pecorino di Pienza. Pick-up and drop-off from your hotel or apartment in Siena are included.
What's included
Included
- Alcoholic beverages
- Free Visit of Pienza
- Free Visit of Montalcino
- Cheese tasting in a Bottega in Pienza
- Typical tuscan lunch + wine tasting + visit of a winery
Not included
- Gratuities
What you'll see and do
Montalcino
Montalcino is a hill town and comune in the province of Siena, Tuscany, central Italy. The town is located to the west of Pienza, close to the Crete Senesi in Val d'Orcia.
60 minutes here
Paradiso di Cacuci Winery
The land destined for the production of Brunello di Montalcino is all around the cellars and tasting rooms, are located a few kilometers from the Montalcino town, about 350 meters above sea level and overlook of Val d'Orcia area.
120 minutes here · Admission included
Historic Centre of the City of Pienza
Visit this UNESCO world Heritage site, snap hundreds pictures of the Val d'Orcia Valley and enjoy a stroll in the nerrow streets of Pienza with maybe an Ice cream in your hands.
60 minutes here · Admission included
Where it starts and ends
Meeting point
Siena
Hotel pickup
Pickup is available for selected locations. Pickup begins about 5 minutes before departure.
Ends at
Returns to the starting point
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, it, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 8 travelers per booking
- Operated by
- Tuscany Private Tour
Know before you go
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Specialized infant seats are available
- Suitable for all physical fitness levels
- Please advise any specific dietary requirements at time of booking
Photos






What travelers are saying
Outty’s summary of the themes that recur across 3 traveler reviews. Written by us, not quoted from reviewers.
The guide
3 mentionsTravelers single out the guide as the reason the experience works.
Food and drink
3 mentionsThe tastings and food stops are a highlight for most reviewers.
Knowledge and storytelling
2 mentionsReviewers describe the commentary as informative rather than scripted.
Photo opportunities
1 mentionThe views and photo stops come up again and again.
Value for money
1 mentionTravelers feel they got more than they paid for.
Traveler reviews
3 verified traveler reviews for Private Montalcino and Pienza Tour from Siena. Ratings and reviews provided by Viator and Tripadvisor.
The city of Piensa was...
The city of Piensa was charming the cheese tasting was 3 pcs and good bye Walked around for a hour no guide tour or suggestions where to go The wine tasting and lunch was fantastic bought wine Then for some reason our driver definitely not a guide decided to take us back to siena and skip Montacino altogether. Trip not worth price
Response from the operator: Dear Louis, Thank you for taking the time to provide your review. I regret to hear that the tour did not meet your expectations and that there were discrepancies between what you expected and what was booked. Typically, this is one of our most appreciated tours. As outlined in the description, the itinerary included free time in Pienza rather than a guided visit. Regarding Montalcino, our driver mentioned you requested an early return to the hotel to pack your bags at leisure; perhaps this was a misunderstanding that could have been clarified through direct and immediate communication. We appreciate your feedback and hope to improve future experiences.
via Viator
Tuscany in a day.
Our tour guide was knowledgeable and helpful with our experience today. Our drive was relaxing and breathtaking on the views of the countryside. Tuscany can’t be explained in pictures. The winery, Cordella for lunch was the best experience I have ever had in all my years visiting wineries!! Was worth every dollar we spent!
Response from the operator: Buongiorno and thank you so much for this great review! We are so happy to know you enjoyed your day and well know that Francesco is a great driver guide. Cordella is a magic place! Hope to see you soon again in Tuscany!
via Viator
Very worthwhile!
Our tour guide, whose name was Tomasa was absolutely wonderful. Very knowledgeable very friendly sense of humor recommendation. Highly recommend him. Loved tasting. Absolutely adorable. Just the right amount of time. I highly recommend this tour!
via Viator
Good to know
- Duration
- 6 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- Available for selected locations
- Booked in 30 days
- 1
- Verdict
- Worth a Look
Who runs this experience
Operated by Tuscany Private Tour, who run 22 experiences we rank across 3 cities, with an average Outty Ranking of 51.2.
See everything Tuscany Private Tour runsWhy this scores 52
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Montalcino and Pienza Tour from Siena: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Siena.
How much does Private Montalcino and Pienza Tour from Siena cost?
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Prices start at $533 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 Private Montalcino and Pienza Tour from Siena take?
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Plan for about 6 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 Private Montalcino and Pienza Tour from Siena worth it?
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It holds an Outty Ranking of 52 out of 100, which we label "Worth a Look". That score blends traveler sentiment (4/5 across 3 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 Private Montalcino and Pienza Tour 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 Private Montalcino and Pienza Tour from Siena suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 6-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Montalcino and Pienza Tour from Siena?
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Around 1 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 6-hour experience runs outdoors or after sunset.
Where does Private Montalcino and Pienza Tour 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, Siena: A Wine Tour and Tasting Experience, Small-Group Montepulciano and Pienza Day Trip from Siena. 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.
What is included in Private Montalcino and Pienza Tour from Siena?
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Included: Alcoholic beverages; Free Visit of Pienza; Free Visit of Montalcino; Cheese tasting in a Bottega in Pienza; and Typical tuscan lunch + wine tasting + visit of a winery. Not included: Gratuities. Always check the voucher for the final list before you travel.
Does Private Montalcino and Pienza Tour from Siena include hotel pickup?
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Yes, pickup is offered, or you can meet at the start point instead from 20 listed pickup locations in and around Siena. Be ready about 5 minutes before the start time. You can also enter a custom pickup address when booking.
What languages is Private Montalcino and Pienza Tour from Siena offered in?
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It is offered in English, Italian and Spanish. Pick your language when choosing a date and time, as not every departure runs in every language.
Will I get instant confirmation and a mobile ticket for Private Montalcino and Pienza Tour from Siena?
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Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.
Is Private Montalcino and Pienza Tour from Siena wheelchair or stroller accessible?
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The operator notes: Infants and small children can ride in a pram or stroller; and Specialized infant seats are available. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to Private Montalcino and Pienza Tour from Siena if the weather is bad?
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It generally runs rain or shine, so dress for the forecast in Siena. Standard cancellation terms apply: free cancellation up to 24 hours before the start.
What do travelers say about Private Montalcino and Pienza Tour from Siena?
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Across 3 reviews averaging 4.0 out of 5, recurring themes include the guide, food and drink, knowledge and storytelling. Travelers single out the guide as the reason the experience works.
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