
Private Tuscany Wine Experience from Rome: Montepulciano & Pienza
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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.
Traveler rating
5.0/5
Based on 5 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Tuscany Wine Experience from Rome: Montepulciano & Pienza worth booking?
Private Tuscany Wine Experience from Rome: Montepulciano & Pienza is a 12-hour experience in Rome, Italy, from $1500 per person. It scores 53 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 5 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 53 / 100
- Rating
- 5/5 (5)
- Duration
- 12 hours
- From
- $1500 per person
Leave Rome for a day and discover the beautiful rolling hills of Tuscany on this private full-day tour. Travel through the scenic countryside and reach the famous hilltop town of Montepulciano, known for its medieval str
What you get
- Val d’Orcia scenic drive
- Hotel pickup and drop-off
- Private driver
- Transportation in luxury A/C vehicle
- Wine tasting in Montepulciano
- Free time in Montepulciano
About this experience
Leave Rome for a day and discover the beautiful rolling hills of Tuscany on this private full-day tour. Travel through the scenic countryside and reach the famous hilltop town of Montepulciano, known for its medieval streets, Renaissance buildings and world-famous wine. You will have free time to explore the historic center, visit local wine shops, and enjoy a wine tasting experience in a traditional Tuscan winery where you will taste local wines including the famous Vino Nobile di Montepulciano. After Montepulciano, the tour continues through the stunning Val d’Orcia countryside, a UNESCO World Heritage Site known for its cypress trees, vineyards and postcard landscapes. You will then visit the charming town of Pienza, famous for pecorino cheese and beautiful panoramic views over the Tuscan hills. Here you will have time to walk through the historic streets, visit local food shops and enjoy lunch in a traditional restaurant.
What's included
Included
- Val d’Orcia scenic drive
- Hotel pickup and drop-off
- Private driver
- Transportation in luxury A/C vehicle
- Wine tasting in Montepulciano
- Free time in Montepulciano
- Free time in Pienza
Not included
- Tour guide
- Lunch
- Gratuities
What you'll see and do
Historic Centre of the City of Pienza
Pienza is one of the 4 Unesco sites in the province of Siena, you can admire the small but wonderful historic center.
180 minutes here
Piazza Grande a Montepulciano
Piazza Grande in Montepulciano is certainly to be counted among the most beautiful squares in Italy, all the main historic buildings of Montepulciano and the Pozzo dei Grifi and dei Leoni overlook it
180 minutes here
Torre del Pulcinella
The statue of Pulcinella in Montepulciano, built in wood and covered in sheet metal, is located on a tower that is part of the church of Sant'Agostino and regularly strikes the hour on a bell. The tower overlooks Piazza Michelozzo di Bartolomeo, the Florentine architect who designed the façade.
180 minutes here
Icario Winery
Icario Winery is a beautiful winery located in the rolling hills near Montepulciano. The winery is built into the hillside and features an underground cellar, modern architecture and panoramic views over the Tuscan countryside. Guests can enjoy a guided wine tasting of Vino Nobile di Montepulciano and other local wines, often paired with extra virgin olive oil and traditional Tuscan products.
60 minutes here · Admission included
Where it starts and ends
Hotel pickup
Pickup is included for all travelers.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- Fattori Car Service
Know before you go
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Specialized infant seats are available
- Suitable for all physical fitness levels
- Please note this tour provides only a chauffeur who is not a professional and licensed guide.
Photos



Traveler reviews
5 verified traveler reviews for Private Tuscany Wine Experience from Rome: Montepulciano & Pienza. Ratings and reviews provided by Viator and Tripadvisor.
The best customer service ever!!
It was actually the best service I ever took. Since the beginning they were really nice, available and definitely helpful. I loved they way they could be really professional and funny at the same time. I would definitely recommend to everyone will need a service like this.
via Tripadvisor
Excellent
My partner and I hired their services for a trip to Tuscany. Great service and attention, highly recommended!
via Tripadvisor
Good to know
- Duration
- 12 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 2
- Verdict
- Worth a Look
Why this scores 53
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Tuscany Wine Experience from Rome: Montepulciano & Pienza: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Rome.
How much does Private Tuscany Wine Experience from Rome: Montepulciano & Pienza cost?
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Prices start at $1500 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Rome usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Private Tuscany Wine Experience from Rome: Montepulciano & Pienza take?
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Plan for about 12 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 Rome is not rushed.
Is Private Tuscany Wine Experience from Rome: Montepulciano & Pienza worth it?
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It holds an Outty Ranking of 53 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 5 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Rome, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Tuscany Wine Experience from Rome: Montepulciano & Pienza?
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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 Tuscany Wine Experience from Rome: Montepulciano & Pienza suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 12-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Tuscany Wine Experience from Rome: Montepulciano & Pienza?
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Around 2 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 Rome 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 Rome and add a light layer if any part of the 12-hour experience runs outdoors or after sunset.
Where does Private Tuscany Wine Experience from Rome: Montepulciano & Pienza 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 Rome 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 Rome?
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Rome runs on skip-the-line access. The Colosseum underground, the Vatican before opening, and the catacombs south of the walls all require a licensed operator, and the price gap between the good ones and the rest is smaller than you would expect. We rank by guide credentials, group size and how reliably the promised access actually materialises. On Outty we rank every Rome experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Rome Pasta and Tiramisu Class: Ravioli, Fettuccine & Fine Wine 5*, Pasta Making & Wine Tasting with Dinner in Frascati from Rome, Rome: Pizza & Tiramisu or Gelato Class with Flowing Fine Wine 5*. 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 Rome?
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April, May, September and October. August is hot and half the city is shut. 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 Rome?
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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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