Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch
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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
4.5/5
Based on 17 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch worth booking?
Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch is a 9-hour experience in Florence, Italy, from $301 per person. It scores 57 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 4.5/5 rating across 17 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 57 / 100
- Rating
- 4.5/5 (17)
- Duration
- 9 hours
- From
- $301 per person
Revel in Tuscany’s wine country and hilltop towns on this Privateday trip from Florence. Traveling by luxury minivan with an expert driver-escort, explore the idyllic hill-towns of Montepulciano and Pienza, learn about P
What you get
About this experience
Revel in Tuscany’s wine country and hilltop towns on this Privateday trip from Florence. Traveling by luxury minivan with an expert driver-escort, explore the idyllic hill-towns of Montepulciano and Pienza, learn about Pecorino Cheese in a local dairy and taste this delicious local produce. In Pienza you will also have free time for lunch. To follow visit a selected winery in the Montepulciano area.
What's included
Included
- Visit Montepulciano & Pienza
- Expert English speaking driver-escort
- Transport by air-conditioned Mercedes minivan
- Lunch
- Pecorino Cheese Tasting at local dairy
Not included
- Gratuities
What you'll see and do
Piazza della Repubblica
The tour begins at 8am from the Piazza della Repubblica where you will meet your English speaking driver - escort.
Pass by without stopping
Historic Centre of the City of Pienza
Then you will be driven to a gorgeous rustic Organic Cheese Farm, just outside Pienza and overlooking the Valley and Pienza itself. Here during a tour of the farm and the dairy you’ll learn how the Pecorino cheese is made and aged and you’ll have the opportunity to taste it accompanied by a glass of wine. Then the tour will continue to Pienza - a small town with a high artistic value. You will be given free time to wander around and here you will also have many lunch opportunities (lunch not included).
120 minutes here
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.
- Languages
- en, it, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 8 travelers per booking
- Operated by
- Avventure Bellissime
Know before you go
- Public transportation options are available nearby
- Specialized infant seats are available
- Travelers should have at least a moderate level of physical fitness
- Comfortable shoes are recommended
- Appropriate dress is required to enter some sites - knees and shoulders must be covered
- Minimum drinking age is 18 years
- Children must be accompanied by an adult
- Infant seats are available on request if advised at time of booking (children who are under 36 kg/97 pounds or 150 cm/4ft 9 in,must use proper child restraints). We reserve the right to refuse infants or children if we are not notified at the time of the booking and if the car seats brought do not comply with requirements by Italian law.
- Operates in all weather conditions, please dress appropriately
- Minimum numbers apply. There is a possibility of cancellation after confirmation if there is not enough passengers to meet requirements. In the event of this occurring, you will be offered an alternative or full refund
- All passengers pay the same rate irrespectively from their age
Photos
What travelers are saying
Outty’s summary of the themes that recur across 17 traveler reviews. Written by us, not quoted from reviewers.
The guide
8 mentionsTravelers single out the guide as the reason the experience works.
Food and drink
8 mentionsThe tastings and food stops are a highlight for most reviewers.
Knowledge and storytelling
5 mentionsReviewers describe the commentary as informative rather than scripted.
Photo opportunities
4 mentionsThe views and photo stops come up again and again.
Small groups
3 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
17 verified traveler reviews for Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch. Ratings and reviews provided by Viator and Tripadvisor.
Honeymoon In Tuscany
Truly the best day of our Honeymoon. Yaris was a pleasure. Very intelligent and friendly, couldn’t have asked for a better experience.
via Tripadvisor
Avoid this company
We had a nice tour of the Ligurian coast with this company and thought they'd be good to go with a second time. We had a much worse tour with a different guide but the same company the next day. Our 'tour guide' was really just a driver, he barely spoke to us, and didn't seem to speak much English anyway. He also drove slow, we were late and missed our second wine tasting out of two. He didn't seem to know our schedule and we seemed to spend more time driving than anything else. Also they made us pay extra at the end of the day for that privilege, demanding 70 euro cash when we got out. DO NOT make the mistake of dealing with this company. If you have to deal with this company, try not to get stuck with Giovanni.
Response from the operator: Dear Client, Thank you for your feedback and I start with saying that I’m glad you’ve enjoyed the Cinque Terre Private tour. In regards to the tour for which you’ve expressed your disappointmet, I must say that I personally worked with your agent on building this itinerary but my proposal included at the beginning a wine tasting within a castle resort where you would have also had your tasting lunch and sightseeing, with time for quick dinner, if required in a town like monteriggioni on the way back to Florence. The tour has been planned to last about 12 hrs starting at 10am. We went back and forth with the planning as apparently you wanted to include two wine tastings, then choose to have lunch not at the castle resort but in a restaurant in Montalcino and wanted to add a wine tasting and also dinner on the way back to Florence in a winery in the Chianti. My error, I admit, was to accept this type of tour de force with too many scheduled events during the day. The day started with a little delay as not all of you were ready for pick up at the stated time and as that day it was also raining , delays have built up during the day – Giovanni, whose english is not perfect but he’s lived in United states and has an american wife, does speak english. He’s not a guide but a driver that can deliver general information on the area. His “ mistake” has been probably not to be too forceful in saying that due to the delay built up ( time spent in Montalcino restaurant – about 2 hrs ), at that point you had to choose if to go to Pienza and skip the second winery or viceversa, he tried to accomplish all program as one of the participants really wanted to go to Pienza. Bottom line, also dinner has been included but of course the second wine tasting was not for the reasons above explained. Giovanni reported that all participants were Ok in skipping the dinner has they had a big lunch, except from one person that wanted to have dinner as well. The tour was meant to finish back to Florence at 10pm, but in fact the arrival in florence was not earlier than 11.15pm . That’s why it was asked a little fee ( 10 € per person ) to cover Giovanni extra time. The long explanation was necessary. Of course bottom line is that I’m very sorry you did not enjoy the tour and I’d like to understand if all 7 people had the same point of view as Giovanni received also a tip at the end of the day. I take on my responsibility for this Day ( I should have been more forceful in saying what was feasable and what not ) and I hope you will give Avventure Bellissime another chance if you come back to Italy. Kind Regards Monica
via Tripadvisor
Fun Time Tasting Cheese and Wine!
My husband and I had the best private tour of Tuscany eating amazing cheese and tasting incredible wine! Our guide Jonathan was enthusiastic and great company while we drove through beautiful towns in Tuscany! He was incredibly knowledgeable and engaging while showing us around the beautiful landscapes. We are very happy with this tour and would highly recommend it to anyone looking to have a wonderful day learning about the architecture of the towns in Tuscany and about winemaking!! Thank you so very much Jonathan!
via Viator
Tuscany beauty
Yaris, our guide, was superb. Friendly, fun, knowledgeable and helpful. Views of Tuscany breathtaking. Towns views were Pienza and Monticello which were picture postcard pretty
via Viator
Wonderful Experience!
This was an excellent tour of the southern Tuscany region. Montepulciano, Pienza, and Montalcino. The winery lunch and conversation was the best I’ve ever had.
via Viator
Good to know
- Duration
- 9 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $301 to $693
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 6
- Verdict
- Worth a Look
Why this scores 57
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch cost?
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Prices start at $301 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 Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch take?
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Plan for about 9 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 Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch worth it?
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It holds an Outty Ranking of 57 out of 100, which we label "Worth a Look". That score blends traveler sentiment (4.5/5 across 17 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 Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch?
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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 Tour: Pienza, Montepulciano Wine Tasting & Lunch suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 9-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch?
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Around 6 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 9-hour experience runs outdoors or after sunset.
Where does Private Tuscany Tour: Pienza, Montepulciano Wine Tasting & Lunch 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 Tales - guided by a STORYTELLER, Florence Pizza or Pasta Class & Gelato Making at a Tuscan Farm, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner. 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.
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