
Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA
Pick your date
Highlighted days have spots open. Grey days are sold out or not running.
September 2026
Loading live availability
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.
Non-refundable booking. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 37 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA worth booking?
Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA is a 8-hour experience in Siena, Italy, from $170 per person. It scores 69 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 5/5 rating across 37 reviews. This booking is non-refundable, so pick your date carefully. Same-day spots are currently showing.
- Outty Ranking
- 69 / 100
- Rating
- 5/5 (37)
- Duration
- 8 hours
- From
- $170 per person
* Only small, authentic, family-run activities * Off-the-beaten path itineraries * Private, exclusive, customizable, flexible, door-to-door tour of Pienza, Val d'Orcia, Montalcino * Local, small wineries for private visi
What you get
- Private transportation
- Bottled water
- On-board WiFi
- Door-to-door pick-up and drop-off
- In-vehicle air conditioning
About this experience
* Only small, authentic, family-run activities * Off-the-beaten path itineraries * Private, exclusive, customizable, flexible, door-to-door tour of Pienza, Val d'Orcia, Montalcino * Local, small wineries for private visit and wine tastings * 8 hours * Very knowledgeable English speaking local drivers
What's included
Included
- Private transportation
- Bottled water
- On-board WiFi
- Door-to-door pick-up and drop-off
- In-vehicle air conditioning
Not included
- Eventual entrance fees
- Lunch
- Gratuities
- Alcoholic beverages
What you'll see and do
Azienda Agricola Capanna di Cencioni
Wine tour and tasting
90 minutes here · Admission included
Montalcino
Passing by Montalcino town
Pass by without stopping
Pienza
Self guided visit of the town of the Pope Pius the 2nd
30 minutes here
Val D'Orcia
Panoramic backroads and picture shooting viewpoints UNESCO sight
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






Good to know
- Duration
- 8 hours
- Free cancellation
- Non-refundable
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $170 to $550
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 13
- Verdict
- Solid Choice
Who runs this experience
Operated by We Drive You Tuscany, who run 12 experiences we rank across 3 cities, with an average Outty Ranking of 43.2.
See everything We Drive You Tuscany runsWhy this scores 69
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Siena.
How much does Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA cost?
+
Prices start at $170 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, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA take?
+
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, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA worth it?
+
It holds an Outty Ranking of 69 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 37 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable family friendly in Siena, and how flexible the cancellation terms are.
Can I cancel or reschedule Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA?
+
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, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA suitable for kids and families?
+
Yes, all ages are welcome. Families should still weigh the 8-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA?
+
Around 13 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?
+
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, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA start and how do I get there?
+
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?
+
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?
+
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?
+
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?
+
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.
Ready to lock in your spot?
Pick a date, choose your group, and see the exact price for Pienza, Val d'Orcia, Montalcino wine and Pecorino cheese PRIVATE TOUR from SIENA.
Pick your date





