Cities, Cheese and Wine Tour in Pienza & Montepulciano in Siena, Italy
Siena, Italy

Cities, Cheese and Wine Tour in Pienza & Montepulciano

Outty Ranking 68 4.9 · 27 traveler reviews6 hoursFrom $570
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Outty Ranking

68/100

Solid Choice. Our proprietary evaluation. How we score

Traveler rating

4.9/5

Based on 27 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Cities, Cheese and Wine Tour in Pienza & Montepulciano worth booking?

Cities, Cheese and Wine Tour in Pienza & Montepulciano is a 6-hour experience in Siena, Italy, from $570 per person. It scores 68 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 4.9/5 rating across 27 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
68 / 100
Rating
4.9/5 (27)
Duration
6 hours
From
$570 per person

Pienza and  Montepulciano Wine Tour - Experiences 1-day exciting trip in Valdorcia Join us for a firsthand look into the wine cellars producing world-class reds, including the famous Nobile di Montepulciano (DOCG) and Super Tuscan, the “king” of Tuscan wines. We can’t wait to show you, your family, or your friends this extraordinary place that we call home. Tour Length: 7/8 hours. Days of Week: Everyday Departure Point: From your accommodation - pick-up and drop-off in Siena, Pienza , Montepulciano, Chianti Area, or South of Siena province. Departure Time: From Siena or nearby 09.00/09.30 AM Note: During this excursion, transport will be made in a Mercedes 9-seat minivan which offers maximum comfort, with air-conditioning, large panoramic windows, and comfortable seats. Unless you don't specify you want to remain private, the experience will be semi-private so max 8 people on a Mercedes minivan Popularity: *****  (best-seller wine and food tour in Tuscany)

What you get

    About this experience

    Pienza and  Montepulciano Wine Tour - Experiences 1-day exciting trip in Valdorcia Join us for a firsthand look into the wine cellars producing world-class reds, including the famous Nobile di Montepulciano (DOCG) and Super Tuscan, the “king” of Tuscan wines. We can’t wait to show you, your family, or your friends this extraordinary place that we call home. Tour Length: 7/8 hours. Days of Week: Everyday Departure Point: From your accommodation - pick-up and drop-off in Siena, Pienza , Montepulciano, Chianti Area, or South of Siena province. Departure Time: From Siena or nearby 09.00/09.30 AM Note: During this excursion, transport will be made in a Mercedes 9-seat minivan which offers maximum comfort, with air-conditioning, large panoramic windows, and comfortable seats. Unless you don't specify you want to remain private, the experience will be semi-private so max 8 people on a Mercedes minivan Popularity: *****  (best-seller wine and food tour in Tuscany)

    What's included

    Included

    • Tasting in a second nobile winery in the afternoon
    • Private transportation
    • Lunch
    • In-vehicle air conditioning
    • Tour and tasting in an historic wine cellar on the Nobile

    Not included

    • Gratuities

    What you'll see and do

    1. Montepulciano

      Visit the village and explore its charming artisan boutiques in the historic center, with the option to enjoy a wine tasting in a traditional underground cellar.

      90 minutes here

    2. Podere Il Casale

      CHEESE FARM LUNCH with a view

      120 minutes here · Admission included

    3. Pienza

      In the afternoon, visit Pienza — stroll through its charming Renaissance streets and end the day with a delicious gelato in the main square.

      90 minutes here

    Where it starts and ends

    Hotel pickup

    Pickup is included for all travelers. Pickup begins about 5 minutes before departure.

    Before you book

    Cancellation
    For a full refund, cancel at least 24 hours before the scheduled departure time.
    Languages
    en
    Ticket
    Mobile Only
    Runs on
    Every day
    Group size
    Up to 15 travelers per booking
    Operated by
    Forzoni Tours

    Know before you go

    • Wheelchair accessible
    • Infants and small children can ride in a pram or stroller
    • Service animals allowed
    • Public transportation options are available nearby
    • Infants are required to sit on an adult’s lap
    • Specialized infant seats are available
    • Transportation options are wheelchair accessible
    • Suitable for all physical fitness levels
    • Luxury air conditioned vehicle – Wifi on board!
    • Pick up and drop off to your hotel or its immediate surroundings
    • English speaking Driver for the day at disposal

    Photos

    Cities, Cheese and Wine Tour in Pienza & Montepulciano in Siena, photo 2Cities, Cheese and Wine Tour in Pienza & Montepulciano in Siena, photo 3Cities, Cheese and Wine Tour in Pienza & Montepulciano in Siena, photo 4Cities, Cheese and Wine Tour in Pienza & Montepulciano in Siena, photo 5Cities, Cheese and Wine Tour in Pienza & Montepulciano in Siena, photo 6Cities, Cheese and Wine Tour in Pienza & Montepulciano in Siena, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 27 traveler reviews. Written by us, not quoted from reviewers.

    Knowledge and storytelling

    8 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Food and drink

    8 mentions

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

    The guide

    6 mentions

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

    Photo opportunities

    2 mentions

    The views and photo stops come up again and again.

    Organization

    2 mentions

    Pickup, timing, and logistics are described as running smoothly.

    Good for families

    2 mentions

    Reviewers traveling with kids report it landed well with their group.

    Traveler reviews

    27 verified traveler reviews for Cities, Cheese and Wine Tour in Pienza & Montepulciano. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    24
    4 star
    3
    3 star
    0
    2 star
    0
    1 star
    0
    Sort
    waynelN9155MW · July 2026

    The cheese farm and tasting was worthwhile for all ages. The wine tour and tasting was worthwhile.

    A working goat and cheese farm interesting for all ages. Even the 5 year old enjoyed it. The winery tour and tasting was very informative and educational. We actually purchased some of their wines t bring home.

    via Tripadvisor

    Meander12719888200 · June 2026

    Tuscany escape

    We had an absolutely wonderful day with Michele exploring Montepulciano, Pienza, and enjoying a beautiful cheese tasting in between. From the moment we met him, it was clear we were in incredibly capable hands. Michele’s knowledge is outstanding — our car rides between stops were filled with fascinating stories, history, and insights that brought the entire region to life. We learned so much more than we ever would have on our own. What really set Michele apart was how thoughtfully he accommodated our small family, including our 3-year-old. He was patient, flexible, and made sure our little one was comfortable and included throughout the day — no small feat on a full day tour! He was friendly, attentive, and punctual at every single stop. If you’re visiting Tuscany and want a guide who combines deep local knowledge with genuine warmth and professionalism, look no further than Michele. We cannot recommend him highly enough — one of the highlights of our entire trip to Italy!

    via Tripadvisor

    bethterhorst · May 2026

    I highly recommend Tours of Tuscany!

    We have actually booked 5 days of tours with this Company. Our driver for two of the days was Camilla and she was an excellent driver giving us history lessons and some basic Italian lessons. Today we did an EVOO tasting in the morning, a sheep farm, where they make wonderful cheeses and serve a delicious lunch, afterwards. On the way back to our hotel in Florence we stopped in Pienza for breathtaking views of the walled city. I highly recommend this Company for a fun filled vacation where everything is taken care of for you and you only have to ride in the van. Definitely an enjoyable experience!

    via Tripadvisor

    janeC7104UJ · July 2024

    A good-value holiday if you like to stay in the countryside instead of a hotel or B and B.

    If you want a relaxing but varied holiday in beautiful Tuscany based on a farm with modern facilities and a pool with cooking classes and visits to local towns, this is the right holiday for you. Up to 12 people can stay for either one or two weeks with most meals included. Chauffeur- driven cars with friendly drivers took us to Cortona for dinner at a different restaurant every night and classes in cheesemaking and pasta-making were included. The hostess organised transport and the daily activities into which we had input, especially when there was free time.

    via Tripadvisor

    Sally A · May 2024

    VIP Treatment with a Local Tour Company.

    Niccolo and his team at Tours of Tuscany made our large group experience in Tuscany an unparalleled luxurious once in a lifetime trip. When I stumbled upon this company online a year before our trip, I had no idea that it was the best decision I would ever make in planning a week long vacation for our group of 11 friends and family. This local company pulled out all the stops, beginning with a consultation via video chat six months before the trip and recommending ideas based on the interests of our group. They personalized the tours for us and made our vacation truly stress-free. They arranged for two Mercedes minivans to transport us safely through the countryside, with drivers who were friendly, accommodating and generous with providing recommendations and insights into local life and points of interest. Everyone felt safe and well cared for. Each experience was thoughtfully planned and executed perfectly. They took us to places we wouldn't have found on our own and with VIP treatment. The cheese farm lunch and tour was a highlight of our day traveling in the Val d'Orcia, then the adorable towns of Pienza and Montepulciano.

    via Tripadvisor

    Good to know

    Duration
    6 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
    9
    Verdict
    Solid Choice

    Who runs this experience

    Operated by Forzoni Tours, who run 8 experiences we rank across 3 cities, with an average Outty Ranking of 63.9.

    See everything Forzoni Tours runs

    Why this scores 68

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

    Traveler sentiment (30% weight)88
    Review evidence (18% weight)57
    Booking momentum (14% weight)48
    Value for money (12% weight)24
    Listing quality (10% weight)85
    Local standing (8% weight)61
    Booking flexibility (8% weight)100

    Cities, Cheese and Wine Tour in Pienza & Montepulciano: questions travelers ask

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

    How much does Cities, Cheese and Wine Tour in Pienza & Montepulciano cost?

    +

    Prices start at $570 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 Cities, Cheese and Wine Tour in Pienza & Montepulciano take?

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    Plan for about 6 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 Cities, Cheese and Wine Tour in Pienza & Montepulciano worth it?

    +

    It holds an Outty Ranking of 68 out of 100, which we label "Solid Choice". That score blends traveler sentiment (4.9/5 across 27 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in Siena, and how flexible the cancellation terms are.

    Can I cancel or reschedule Cities, Cheese and Wine Tour in Pienza & Montepulciano?

    +

    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 Cities, Cheese and Wine Tour in Pienza & Montepulciano suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 6-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Cities, Cheese and Wine Tour in Pienza & Montepulciano?

    +

    Around 9 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 6-hour experience runs outdoors or after sunset.

    Where does Cities, Cheese and Wine Tour in Pienza & Montepulciano 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, Siena: A Wine Tour and Tasting Experience, Small-Group Montepulciano and Pienza Day Trip from Siena. 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?

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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 Cities, Cheese and Wine Tour in Pienza & Montepulciano?

    +

    Included: Tasting in a second nobile winery in the afternoon; Private transportation; Lunch; In-vehicle air conditioning; and Tour and tasting in an historic wine cellar on the Nobile. Not included: Gratuities. Always check the voucher for the final list before you travel.

    Does Cities, Cheese and Wine Tour in Pienza & Montepulciano include hotel pickup?

    +

    Yes, pickup is offered for every traveler from 337 listed pickup locations in and around Siena. Be ready about 5 minutes before the start time. You can also enter a custom pickup address when booking.

    What languages is Cities, Cheese and Wine Tour in Pienza & Montepulciano offered in?

    +

    It runs in English. 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 Cities, Cheese and Wine Tour in Pienza & Montepulciano?

    +

    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 Cities, Cheese and Wine Tour in Pienza & Montepulciano wheelchair or stroller accessible?

    +

    The operator notes: Wheelchair accessible; Infants and small children can ride in a pram or stroller; Infants are required to sit on an adult’s lap; and Specialized infant seats are available. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.

    What happens to Cities, Cheese and Wine Tour in Pienza & Montepulciano if the weather is bad?

    +

    It generally runs rain or shine, so dress for the forecast in Siena. Standard cancellation terms apply: free cancellation up to 24 hours before the start.

    What do travelers say about Cities, Cheese and Wine Tour in Pienza & Montepulciano?

    +

    Across 27 reviews averaging 4.9 out of 5, recurring themes include knowledge and storytelling, food and drink, the guide. Reviewers describe the commentary as informative rather than scripted.

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