
Small Group Tuscany Trip from Rome: Pienza and Montepulciano
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September 2026
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Who is going?
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 3 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Small Group Tuscany Trip from Rome: Pienza and Montepulciano worth booking?
Small Group Tuscany Trip from Rome: Pienza and Montepulciano is a 12-hour experience in Rome, Italy, from $50 per person. It scores 63 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 5/5 rating across 3 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 63 / 100
- Rating
- 5/5 (3)
- Duration
- 12 hours
- From
- $50 per person
Enjoy a wonderful day in the vineyards of Tuscany, a region famous for its fine wines. You will be picked up at your hotel or apartment in Rome and head to the beautiful Val D'Orcia area. Your first stop on the tour will
What you get
- Pick up and drop off
- Assistant for the entire duration of the tour
- Driver
- Wine tasting and local products in a historic winery
About this experience
Enjoy a wonderful day in the vineyards of Tuscany, a region famous for its fine wines. You will be picked up at your hotel or apartment in Rome and head to the beautiful Val D'Orcia area. Your first stop on the tour will be Montepulciano, a picturesque medieval town renowned for its vineyards and the famous Nobile di Montepulciano wine. Stroll through the cobbled streets and sample fine local wines during a tasting in a historic winery located in the city center. After exploring Montepulciano, continue to Pienza, a jewel of the Tuscan Renaissance. Here, you can admire the splendid architecture, visit the Cathedral of Pienza and stroll through the charming streets of the historic center. Do not miss the opportunity to taste the pecorino di Pienza, one of the most delicious cheeses in the region. After this unforgettable experience, return to Rome with precious memories of a day of history, culture and authentic flavors.
What's included
Included
- Pick up and drop off
- Assistant for the entire duration of the tour
- Driver
- Wine tasting and local products in a historic winery
Not included
- Gratuities
- Lunch
What you'll see and do
Montepulciano
Montepulciano, a charming hill town located in the heart of Tuscany, is famous for its fine wines, such as Vino Nobile di Montepulciano. This medieval town, surrounded by vineyards and olive groves, offers breathtaking panoramic views of the Tuscan countryside. Walking through the narrow streets of Montepulciano, you will discover fascinating historic buildings, such as the Town Hall and the Cathedral of Santa Maria Assunta. The city is also renowned for its wineries, many of which are located in ancient basements, where you can taste some of the best wines in the region. Montepulciano is an ideal place to immerse yourself in Tuscan culture, history and wine tradition.
120 minutes here
Pienza
Pienza, located in the heart of the Val d'Orcia in Tuscany, is a pearl of the Italian Renaissance. Designed by architect Bernardo Rossellino at the behest of Pope Pius II, the city is a perfect example of Renaissance urban planning. Walking through its narrow streets, you can admire beautiful buildings such as the Cathedral of Pienza. The town also offers breathtaking views of the surrounding countryside, characterized by rolling hills and vineyards. Do not miss the opportunity to taste the famous pecorino cheese of Pienza, a sheep cheese appreciated all over the world.
60 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers. Pickup begins about 10 minutes before departure.
Options you can book
PRIVATE TOUR
Private Tour: The private tour is wheelchair accessible. Pickup included
SMALL GROUP TOUR
Tour for small groups : The small group tour is not wheelchair accessible. Pickup included
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- pt, en, fr, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 12 travelers per booking
- Operated by
- Mamma Mia Italia
Know before you go
- Infants and small children can ride in a pram or stroller
- Specialized infant seats are available
- Suitable for all physical fitness levels
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
2 mentionsTravelers single out the guide as the reason the experience works.
Food and drink
2 mentionsThe tastings and food stops are a highlight for most reviewers.
Knowledge and storytelling
1 mentionReviewers describe the commentary as informative rather than scripted.
Photo opportunities
1 mentionThe views and photo stops come up again and again.
Traveler reviews
3 verified traveler reviews for Small Group Tuscany Trip from Rome: Pienza and Montepulciano. Ratings and reviews provided by Viator and Tripadvisor.
Montepulciano and Pienza tour
Our guide Michaela was amazing! She was so informative and recommended so many places along the way and near our hotel. They brought us to an amazing vineyard and showed us amazing views in Montepulciano and Pienza. Highly recommend!!
Response from the operator: Thank you so much for your wonderful review! We’re delighted to hear that Michela made your experience so enjoyable with her knowledge, helpful recommendations, and attention to detail. We’re also happy that you enjoyed the vineyard and the beautiful scenery of Montepulciano and Pienza. Thank you for your recommendation, and we hope to welcome you again for another unforgettable experience in Italy!
via Viator
Amazing Montepulciano and Pienza Day Tour!
Our tour with Michaela and Max was exceptional! We took a tour to Montepulciano and Pienza and it included the perfect wine tour. It was a perfect way to spend our day exploring the most quaint little towns in Tuscany! Thank you for making our day so memorable!
Response from the operator: Thank you so much for your wonderful review! We’re delighted to hear that Michela and Max made your experience in Montepulciano and Pienza so special. We’re happy that you enjoyed the wine tour and the charm of the beautiful Tuscan villages. Your kind words mean a lot to us, and we hope to welcome you again soon for another unforgettable experience in Italy!
via Tripadvisor
A countryside delight
Max , Martina and Carola were excellent. Max was a steady safe non exasperated driver , funny too. Martina keep a great schedule so there was no rushing or unnecessary down time. When she and Carola got to describing the sites it was magical. The wine tasting was lovely. Well thought out and of course the vino 🍷 yummy. Great break out of hustle and bustle of Rome
Response from the operator: Thank you so much for the lovely review! We’re happy to hear that Max, Martina, and Carola helped make the experience special, with magical stories and excellent wine. A special thank you from them as well. We hope to see you again soon for another adventure together!
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
- Price range
- $50 to $1134
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 1
- Verdict
- Solid Choice
Why this scores 63
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Small Group Tuscany Trip from Rome: Pienza and Montepulciano: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Rome.
How much does Small Group Tuscany Trip from Rome: Pienza and Montepulciano cost?
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Prices start at $50 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 Small Group Tuscany Trip from Rome: Pienza and Montepulciano 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 Small Group Tuscany Trip from Rome: Pienza and Montepulciano worth it?
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It holds an Outty Ranking of 63 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 3 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 Small Group Tuscany Trip from Rome: Pienza and Montepulciano?
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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 Small Group Tuscany Trip from Rome: Pienza and Montepulciano 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 Small Group Tuscany Trip from Rome: Pienza and Montepulciano?
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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 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 Small Group Tuscany Trip from Rome: Pienza and Montepulciano 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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