Pienza and Montepulciano Private Wine Tour in Florence, Italy
Florence, Italy

Pienza and Montepulciano Private Wine Tour

Outty Ranking 528 hoursFrom €340
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Outty Ranking

52/100

Worth a Look. Our proprietary evaluation. How we score

Traveler rating

Not yet rated

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Quick answer

Is Pienza and Montepulciano Private Wine Tour worth booking?

Pienza and Montepulciano Private Wine Tour is a 8-hour experience in Florence, Italy, from €340 per person. It scores 52 out of 100 on the Outty Ranking, which we label “Worth a Look”. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
52 / 100
Rating
Not yet rated
Duration
8 hours
From
€340 per person

Experience a full day private tour in Pienza and Montepulciano, exploring the UNESCO World Heritage site of Val d'Orcia, celebrated for its stunning beauty and nature. Your adventure begins with a morning pickup from your accommodation by our driver. Discover the renowned cities of Montepulciano and Pienza in a unique way by exploring their underground attractions. In Pienza, visit the crypt and labyrinth, then stroll along charming streets like Via del Bacio. Next, head to Montepulciano for a panoramic view at the Church of San Biagio before descending into the underground city, which connects seven historic buildings and features the Well of Love. The tour concludes with a tasting of Montepulciano's prestigious wine.

What you get

    About this experience

    Experience a full day private tour in Pienza and Montepulciano, exploring the UNESCO World Heritage site of Val d'Orcia, celebrated for its stunning beauty and nature. Your adventure begins with a morning pickup from your accommodation by our driver. Discover the renowned cities of Montepulciano and Pienza in a unique way by exploring their underground attractions. In Pienza, visit the crypt and labyrinth, then stroll along charming streets like Via del Bacio. Next, head to Montepulciano for a panoramic view at the Church of San Biagio before descending into the underground city, which connects seven historic buildings and features the Well of Love. The tour concludes with a tasting of Montepulciano's prestigious wine.

    What's included

    Included

    • Multilingual driver
    • Traditional lunch
    • Entrance and visit to the Underground City of Montepulciano with wine tasting included
    • Entrance and free visit to the Crypt of Pienza including two levels of the Underground Labyrinth
    • Pick up and drop off at the Hotel
    • Stop at the Church of San Biagio di Montepulciano

    Not included

    • Gratuities (optional)

    What you'll see and do

    1. Pienza

      Explore the Crypt of Pienza, which features two levels of an intriguing Underground Labyrinth. Here, you’ll learn about the history of the crypt and admire its unique architecture. After the visit, take a stroll along Via del Bacio, enjoying the charming streets of Pienza.

      60 minutes here

    2. Church of San Biagio Vescovo

      Stop at the Church of San Biagio, a beautiful Renaissance church offering panoramic views of the surrounding countryside. Learn about its architectural significance and enjoy the serene atmosphere before continuing your journey to Montepulciano.

      60 minutes here

    3. Montepulciano

      Descend into the Underground City of Montepulciano, where you'll explore tunnels connecting seven historical buildings. This fascinating journey includes viewing the Well of Love and learning about the historical significance of the underground structures. The tour concludes with a tasting of Montepulciano's prestigious wines, enhancing your experience of this remarkable location.

      120 minutes here

    4. Duomo

      Discover the underground wonders of Pienza by visiting the crypt and underground labyrinth, spread across two levels. You’ll also have time to stroll through the charming streets of Pienza, such as the famous Via del Bacio.

      60 minutes here · Admission included

    Where it starts and ends

    Hotel pickup

    Pickup is included for all travelers. Pickup begins about 15 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 15 travelers per booking
    Operated by
    myTour in Italy

    Know before you go

    • Public transportation options are available nearby
    • Infants are required to sit on an adult’s lap
    • Not recommended for travelers with spinal injuries
    • Not recommended for pregnant travelers
    • Not recommended for travelers with poor cardiovascular health
    • Suitable for all physical fitness levels
    • We can accommodate dietary restrictions such as vegetarian, vegan, gluten-free, etc. If you have dietary requirements, please indicate them when booking.
    • Note: The remaining time in the tour will be allocated for pick-up and drop-off transport, the visit to the crypt of Pienza, and the wine tasting. Each stop has been timed to ensure you have ample time to enjoy all the attractions while fitting comfortably within the 8-hour tour.

    Photos

    Pienza and Montepulciano Private Wine Tour in Florence, photo 2Pienza and Montepulciano Private Wine Tour in Florence, photo 3Pienza and Montepulciano Private Wine Tour in Florence, photo 4Pienza and Montepulciano Private Wine Tour in Florence, photo 5Pienza and Montepulciano Private Wine Tour in Florence, photo 6Pienza and Montepulciano Private Wine Tour in Florence, photo 7

    Traveler reviews

    1 verified traveler reviews for Pienza and Montepulciano Private Wine Tour. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    0
    4 star
    0
    3 star
    0
    2 star
    0
    1 star
    1
    dylanabroad · October 2026

    Truly a Scam - Group Size was Twice the Maximum Listed

    I did this tour with two friends and SIXTY other people, even though the site said it was maximum thirty people. I'm sure everyone enjoys sixty people crammed into a wine cellar. On top of that it was very sparse in wine sample and wine information. The price is nowhere near worth the quality. I'm not sure what Mattia did, because we only heard him introduce himself then disappear. Sofi read from a script and did not seem to have anything to make this tour more interesting than a Lonely planet chapter on Tuscan wines. Their company refused any refund even though Sofia suggested that as how to fix this. Will never book again.

    via Tripadvisor

    Good to know

    Duration
    8 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Every day
    Price range
    €340 to €790
    Hotel pickup
    Included for all travelers
    Booked in 30 days
    0
    Verdict
    Worth a Look

    Who runs this experience

    Operated by myTour in Italy, who run 51 experiences we rank across 5 cities, with an average Outty Ranking of 57.8.

    See everything myTour in Italy runs

    Why this scores 52

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

    Traveler sentiment (30% weight)77
    Review evidence (18% weight)0
    Booking momentum (14% weight)0
    Value for money (12% weight)68
    Listing quality (10% weight)83
    Local standing (8% weight)50
    Booking flexibility (8% weight)100

    Pienza and Montepulciano Private Wine Tour: questions travelers ask

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

    How much does Pienza and Montepulciano Private Wine Tour cost?

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    Prices start at €340 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Florence usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does Pienza and Montepulciano Private Wine Tour take?

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    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 Florence is not rushed.

    Is Pienza and Montepulciano Private Wine Tour 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 (0/5 across 0 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Florence, and how flexible the cancellation terms are.

    Can I cancel or reschedule Pienza and Montepulciano Private Wine Tour?

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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 Pienza and Montepulciano Private Wine Tour suitable for kids and families?

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    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 and Montepulciano Private Wine Tour?

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    Around 0 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 Florence 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 Florence and add a light layer if any part of the 8-hour experience runs outdoors or after sunset.

    Where does Pienza and Montepulciano Private Wine Tour 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 Florence 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 Florence?

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    On Outty we rank every Florence experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Best tour in Florence: Renaissance & Medici -by a storyteller, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner, Florence Pizza or Pasta Class with Gelato Making at a Tuscan Farm. 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 Florence?

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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 Florence?

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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 Pienza and Montepulciano Private Wine Tour?

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    Included: Multilingual driver; Traditional lunch; Entrance and visit to the Underground City of Montepulciano with wine tasting included; Entrance and free visit to the Crypt of Pienza including two levels of the Underground Lab; and Pick up and drop off at the Hotel. Not included: Gratuities (optional). Always check the voucher for the final list before you travel.

    Does Pienza and Montepulciano Private Wine Tour include hotel pickup?

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    Yes, pickup is offered for every traveler from 578 listed pickup locations in and around Florence. Be ready about 15 minutes before the start time. You can also enter a custom pickup address when booking.

    What languages is Pienza and Montepulciano Private Wine Tour 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 Pienza and Montepulciano Private Wine Tour?

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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 Pienza and Montepulciano Private Wine Tour wheelchair or stroller accessible?

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    The operator notes: Infants are required to sit on an adult’s lap; and Not recommended for pregnant travelers. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.

    What happens to Pienza and Montepulciano Private Wine Tour if the weather is bad?

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    This experience depends on good weather. If it is canceled because of poor weather, you are offered a different date or a full refund.

    Ready to lock in your spot?

    Pick a date, choose your group, and see the exact price for Pienza and Montepulciano Private Wine Tour.

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