Private Tuscany Wine Tour from Rome Montepulciano and Pienza in Rome
Rome, Italy

Private Tuscany Wine Tour from Rome Montepulciano and Pienza

Outty Ranking 58 4.2 · 6 traveler reviews10 hoursFrom $148

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September 2026

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Adults

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From, per person$148
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Outty Ranking

58/100

Worth a Look. Our proprietary evaluation. How we score

Traveler rating

4.2/5

Based on 6 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Private Tuscany Wine Tour from Rome Montepulciano and Pienza worth booking?

Private Tuscany Wine Tour from Rome Montepulciano and Pienza is a 10-hour experience in Rome, Italy, from $148 per person. It scores 58 out of 100 on the Outty Ranking, which we label “Worth a Look, based on a 4.2/5 rating across 6 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
58 / 100
Rating
4.2/5 (6)
Duration
10 hours
From
$148 per person

Leave the bustle of Rome behind and enjoy an elegant private journey into the heart of Tuscany. Travel through the scenic Crete Senesi and the rolling hills of Montepulciano and Pienza, where vineyards, historic villages

What you get

    About this experience

    Leave the bustle of Rome behind and enjoy an elegant private journey into the heart of Tuscany. Travel through the scenic Crete Senesi and the rolling hills of Montepulciano and Pienza, where vineyards, historic villages, and breathtaking countryside create an unforgettable setting. Visit a prestigious local winery and enjoy a guided tasting of Vino Nobile di Montepulciano, regional wines, Vin Santo, artisanal Pecorino cheeses, and extra-virgin olive oil, all fresh and locally produced. Stroll through charming Pienza and immerse yourself in authentic Tuscan beauty, flavors, and relaxed elegance—perfect for couples, families, and wine lovers seeking a refined day trip from Rome.

    What's included

    Included

    • Exclusive winery experience with guided vineyard and cellar visit
    • Professional English- and Spanish-speaking chauffeur
    • Complimentary hotel pickup and drop-off in Rome
    • Private luxury transportation throughout the day
    • Tasting of five carefully selected regional 5 wines

    Not included

    • Lunch and additional beverages beyond the tasting
    • Optional Tuscan tasting platter (€20 per person)
    • Gratuities for your chauffeur, at your discretion
    • Port pickup in Civitavecchia (€100 per group, payable to the driver)

    What you'll see and do

    1. At 8:00 AM, depart from your accommodation in Rome in a luxury vehicle with a professional English- and Spanish-speaking driver. Enjoy a scenic journey into the heart of Tuscany, traveling through the iconic Crete Senesi and rolling green hills with stunning panoramic views. Your first stop is a renowned winery, where an expert sommelier will guide you through the vineyards and historic cellars, sharing the story and traditions of local winemaking. Taste up to five organic wines—including the celebrated Vino Nobile di Montepulciano—paired with extra-virgin olive oil, cured meats, cheeses, bruschetta, Vin Santo, and traditional cantucci. After the tasting, explore the charming medieval streets of Montepulciano. If lunch was not enjoyed at the winery, you may choose to dine at a local restaurant specializing in authentic Tuscan cuisine (not included)

      180 minutes here · Admission included

    2. Montepulciano is a beautiful medieval hilltop town rich in history and tradition, with origins dating back to the Etruscan civilization in the 4th century BC. Surrounded by rolling vineyards, it is world-famous for its prestigious red wine, Vino Nobile. Visitors can admire the iconic Torre di Pulcinella, a historic clock tower topped by Pulcinella, a character from the traditional commedia dell’arte. The main square features the 14th-century Town Hall and the Cathedral, home to an impressive altar triptych, offering a remarkable glimpse into the town’s artistic and cultural heritage.

      30 minutes here

    3. Historic Centre of the City of Pienza

      About Pienza You will visit the charming town of Pienza, nestled in the heart of the prestigious Val d'Orcia countryside. Renowned as an architectural jewel and a treasure of local gastronomy, Pienza is especially famous for its exceptional Pecorino cheese, enjoyed both fresh and aged. In the 15th century, what was once a small fortified hilltop village was transformed by Pope Pius II into an ideal Renaissance town—an ambitious urban vision that still defines its beauty today. You will also have free time to wander through its picturesque streets, scenic viewpoints, and artisan shops, fully experiencing the timeless atmosphere of this enchanting destination.

      45 minutes here

    Where it starts and ends

    Hotel pickup

    Pickup is included for all travelers. Pickup begins about 10 minutes before departure.

    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
    Fast Travel Services

    Know before you go

    • Wheelchair accessible
    • Infants and small children can ride in a pram or stroller
    • Service animals allowed
    • Specialized infant seats are available
    • Transportation options are wheelchair accessible
    • All areas and surfaces are wheelchair accessible
    • Suitable for all physical fitness levels
    • Gli animali devono avere il loro trasportino

    Photos

    Private Tuscany Wine Tour from Rome Montepulciano and Pienza in Rome, photo 2Private Tuscany Wine Tour from Rome Montepulciano and Pienza in Rome, photo 3Private Tuscany Wine Tour from Rome Montepulciano and Pienza in Rome, photo 4Private Tuscany Wine Tour from Rome Montepulciano and Pienza in Rome, photo 5Private Tuscany Wine Tour from Rome Montepulciano and Pienza in Rome, photo 6Private Tuscany Wine Tour from Rome Montepulciano and Pienza in Rome, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 6 traveler reviews. Written by us, not quoted from reviewers.

    The guide

    6 mentions

    Travelers single out the guide as the reason the experience works.

    Knowledge and storytelling

    3 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Photo opportunities

    3 mentions

    The views and photo stops come up again and again.

    Food and drink

    3 mentions

    The tastings and food stops are a highlight for most reviewers.

    Small groups

    3 mentions

    The group size is repeatedly described as intimate rather than packed.

    Value for money

    2 mentions

    Travelers feel they got more than they paid for.

    Traveler reviews

    6 verified traveler reviews for Private Tuscany Wine Tour from Rome Montepulciano and Pienza. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
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    Jordan_W · April 2026

    We had a lovely day out...

    We had a lovely day out with our driver Alex. He was able to show us all we were after and took us to some very beautiful winery’s. Couldn’t ask for a better day.

    Response from the operator: Good morning to you! You are a wonderful family, and thanks to your kind participation, we were able to share much of our experience in Tuscany, a marvelous land that makes everyone who visits fall in love with it. Thank you for your valuable contribution. May we continue our journey and enjoy Europe. Alex

    via Viator

    M4811HAdavido · December 2024

    Good times!

    It was wonderful. The Canneto wine tasting was great. We loved the towns. Could have used more time in Montepulciano. Alessandro was a great guide.

    Response from the operator: Thank you so much for your kind words! Good morning Mr. and Mrs. O'brien, it was a real pleasure to have you as our guests, thanks to your precious collaboration we were able to offer our best. We are happy that you had a great time with the activities offered. Blessings, happy Christmas holidays and many beautiful things for a wonderful year 2025.

    via Tripadvisor

    Ellana_S · May 2024

    Not worth the price

    The winery Canneto and the host Daniela at the winery were the best part. Although Alex, our driver, was a lovely man, he did not speak or understand English or Spanish. We read on a previous review that his English wasn’t great, but figured, since we speak Spanish as well (which it says he does) we’d be fine. Not so much. We were hoping for a private tour, we would have been offered more information, history, anything really…. But Alex was mostly just a driver. Not worth the price

    Response from the operator: Our driver Alessandro sometimes also called Alex, is a very good and helpful driver of ours, he is a new guy and certainly with all the good will he tried to do his best. The real Alex (named Alex) speaks Italian and Spanish at a native level, English very well but not fluent. The tour includes wine tasting in English which would be the most important part of the activity, Alessando's level was sufficient to understand and make the drop-off and pick-up in the small towns to visit understood, maybe some panoramic explanation of the place but not at the level of a tourist guide. The driver acts as a guide because he takes you to make the stops and visits before the main attraction of the service: THE WINE TASTING IN ENGLISH.

    via Viator

    Shannon_M · October 2023

    We were on a cruise and...

    We were on a cruise and took an extra day to leave from Rome to drive to Tuscany. Our driver was very nice, absolutely punctual and very experienced driver. However with limited English and needing to communicate somewhat thru Spanish a very second language to me it was difficult. We drove to the beautiful towns of Pienza and Montepulciano. We were not however prepared to tour the towns and glean any history or knowledge other than pictures on our own. I'm happy we were able to experience Tuscany but would make sure that should we do it again, with someone speaking full English.

    Response from the operator: Thank you for appreciating our tour, sometimes we are inundated with work requests and in any case we try to satisfy all our customers. We are pleased that you appreciated the effort of our assistant and above all his kindness and professionalism. Cordial greetings

    via Viator

    Joanne_A · August 2023

    AMAZING EXPERIENCE: READ PLEASE

    This was the highlight of our stay in Rome. We had initially booked a different tour, and rebooked a private tour when a member of our group had last minute surgery. BEST DECISION we could have made. We agreed that this was well worth the money. We were picked up by our guide Alessandro who from the beginning was prompt, polite and very accommodating to the member of our group that was on crutches. We drove from Rome to Pienza. On the way we stopped a beautiful castle for photos. In Pienza, Alessandro accompanied us and told us about the city, walked around the shops and we tasted delicious cheeses, vinegar and olive oil. We traveled to Montepulciano where we were greeted by Daniela and toured the cellars. Daniela was personable and knowledgeable. The tour was the perfect length and we sampled many, many wines and olive oil. The views from the vineyard were stunning. We could not stop talking about what an amazing day it had been. We ended up purchasing wine and olive oil because it was so delicious. We opted to have lunch at a restaurant (there were some picky eaters in the group), and Alessandro brought us to a lovely restaurant. We do not speak Italian, and Alessandro stayed with us until we ordered to ensure the order was placed correctly. The lunch was absolutely delicious! We really appreciated the kindness and hospitality provided throughout the tour. We traveled as 3 sisters in our late 20’s- early 30’s and our mom who is in her 60’s, and all of us said we would do this again in a heartbeat! I truly cannot recommend this tour enough!

    Response from the operator: Good morning! Three beautiful girls and a beautiful lady, you are a wonderful family! Thank you for your cooperation and kindness, thank you for your sympathy and help which made the day much more dynamic and easier. For us it was a real pleasure to work with you and to have had them as guests! Your precious words fill us with joy and courage to continue offering the best of our services.! We are here, we look forward to seeing you next time, a very dear greeting! Thank you very much! Alessandro

    via Viator

    Good to know

    Duration
    10 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Every day
    Price range
    $148 to $845
    Hotel pickup
    Included for all travelers
    Booked in 30 days
    2
    Verdict
    Worth a Look

    Why this scores 58

    The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

    Traveler sentiment (30% weight)67
    Review evidence (18% weight)27
    Booking momentum (14% weight)17
    Value for money (12% weight)100
    Listing quality (10% weight)79
    Local standing (8% weight)38
    Booking flexibility (8% weight)100

    Private Tuscany Wine Tour from Rome Montepulciano and Pienza: questions travelers ask

    Practical detail on this experience, plus the wider planning questions for Rome.

    How much does Private Tuscany Wine Tour from Rome Montepulciano and Pienza cost?

    +

    Prices start at $148 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 Tour from Rome Montepulciano and Pienza take?

    +

    Plan for about 10 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 Tour from Rome Montepulciano and Pienza worth it?

    +

    It holds an Outty Ranking of 58 out of 100, which we label "Worth a Look". That score blends traveler sentiment (4.2/5 across 6 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 Tour from Rome Montepulciano and Pienza?

    +

    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 Tour from Rome Montepulciano and Pienza suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 10-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Private Tuscany Wine Tour from Rome Montepulciano and Pienza?

    +

    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?

    +

    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 10-hour experience runs outdoors or after sunset.

    Where does Private Tuscany Wine Tour from Rome Montepulciano and 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?

    +

    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?

    +

    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?

    +

    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.

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