Private Montepulciano & Pienza Day Trip from Florence
Pick your date
Highlighted days have spots open. Grey days are sold out or not running.
September 2026
Loading live availability
Who is going?
Adults
Age 13 and over
Children
Age 12 and under
Select a highlighted day to see live departure times and the exact price for your group.
Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
5.0/5
Based on 10 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Montepulciano & Pienza Day Trip from Florence worth booking?
Private Montepulciano & Pienza Day Trip from Florence is a 8-hour experience in Florence, Italy, from $763 per person. It scores 56 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 10 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 56 / 100
- Rating
- 5/5 (10)
- Duration
- 8 hours
- From
- $763 per person
Experience Tuscany on a private full-day Montepulciano and Pienza tour from Florence, traveling in comfort with an English-speaking chauffeur in a luxury Mercedes-Benz vehicle. This itinerary combines medieval towns, wo
What you get
About this experience
Experience Tuscany on a private full-day Montepulciano and Pienza tour from Florence, traveling in comfort with an English-speaking chauffeur in a luxury Mercedes-Benz vehicle. This itinerary combines medieval towns, world-class wine, and iconic Tuscan food traditions. Explore the elegant streets of Montepulciano, enjoy a winery visit featuring the renowned Vino Nobile di Montepulciano, and continue through the Val d’Orcia for a cheese tasting centered around Pecorino di Pienza. Unlike group tours, this experience is fully private and customizable, offering door-to-door service, relaxed pace, and the flexibility to adapt the day to your interests. While visits are unguided, your chauffeur will share local knowledge, history, and cultural insights throughout the journey. Operated by Best Rome Driver, a trusted Italian company with nearly 20 years of experience, this tour guarantees reliability, professionalism, and a high standard of service throughout your day in Tuscany.
What's included
Included
- Private English-speaking chauffeur
- Fully customizable private itinerary
- Luxury Mercedes-Benz sedan or van
- Winery and cheese tasting reservations
- Pickup and drop-off from any Florence location
Not included
- Private Licensed Tour Guides
- Wine tasting fees
- Cheese tasting and lunch
- Gratuities (optional)
What you'll see and do
Florence
Pickup directly from your accommodation or preferred location in Florence. Meet your English-speaking chauffeur, who will be at your disposal for the full day in a luxury Mercedes-Benz sedan or van. During the drive, your chauffeur will share historical context, local traditions, and insights into the Tuscan countryside you’ll be crossing.
Pass by without stopping
Montepulciano
Arrive in Montepulciano, a stunning hilltop town known for its Renaissance palaces, stone streets, and sweeping views over the Val d’Orcia. You’ll have time to stroll through the historic center, explore small shops, and enjoy the atmosphere of one of Tuscany’s most elegant wine towns. Highlights you may see include : Piazza Grande, Historic palazzos and noble residences, Panoramic viewpoints over the countryside
60 minutes here
Montepulciano
After the town visit, meet your driver and continue to a local winery just outside Montepulciano. Here you’ll enjoy a tasting of the area’s most famous wines, including Vino Nobile di Montepulciano, produced from Prugnolo Gentile grapes and known for its structure, elegance, and aging potential. The tasting is typically accompanied by local products such as olive oil or light Tuscan appetizers. Note : Wine tasting is not included and is paid directly at the winery. We reserve the visit in advance.
60 minutes here
Pienza
Continue through the rolling hills of the Val d’Orcia to the Pienza countryside, where you’ll stop at a traditional local cheese factory. Here you can enjoy a tasting and lunch centered around Pecorino di Pienza, one of Tuscany’s most celebrated sheep’s-milk cheeses, often paired with honey, jams, cured meats, and local wine. Pienza is known all over the world for its production of 'pecorino cheese' and for its traditional Tuscan cuisine. Note : Tasting and lunch are not included and are paid directly on site. Reservations are arranged in advance.
120 minutes here
Pienza
In the afternoon, your chauffeur will take you into Pienza itself, a UNESCO World Heritage town designed during the Renaissance as an “ideal city.” Enjoy free time to stroll through its elegant streets, artisan shops, and scenic terraces overlooking the Val d’Orcia. Highlights you may see include : Piazza Pio II, Pienza Cathedral, Panoramic viewpoints over the Val d’Orcia
60 minutes here
Florence
Relax during the scenic drive back to Florence, with drop-off at any location of your choice.
Pass by without stopping
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
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 15 travelers per booking
- Operated by
- Best Rome Driver Private Tours
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
- Suitable for all physical fitness levels
- Foldable wheelchairs only, which must fit in the vehicle trunk
- Guests has to be able to get in and out of the vehicle independently
Photos
What travelers are saying
Outty’s summary of the themes that recur across 10 traveler reviews. Written by us, not quoted from reviewers.
Food and drink
6 mentionsThe tastings and food stops are a highlight for most reviewers.
The guide
5 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
4 mentionsReviewers describe the commentary as informative rather than scripted.
Organization
4 mentionsPickup, timing, and logistics are described as running smoothly.
Photo opportunities
2 mentionsThe views and photo stops come up again and again.
Small groups
2 mentionsThe group size is repeatedly described as intimate rather than packed.
Traveler reviews
10 verified traveler reviews for Private Montepulciano & Pienza Day Trip from Florence. Ratings and reviews provided by Viator and Tripadvisor.
Amazing food, people and tour company!
This was an amazing experience! We toured montepulciano, Pienza and Val d’orcia with peppino and it was the best experience we’ve had so far in Italy! Pep was very kind, friendly and extremely professional. The places we visited were out of this world. The cheese was good! We travelled with our 11 month old son and they provided a car seat! The itinerary was tailored to suit our needs. Very thankful for this tour company and experience!
Response from the operator: Buongiorno, Thank you for your precious review! It's always a pleasure to know that our wonderful clients are satisfied with the services we have provided for them. I'm happy to read that you had awesome time on board with your Professional Driver Peppino! We truly look forward to seeing you for your next vacation in Italy! Best Rome Driver Team
via Tripadvisor
Amazing private tour with Alessandro
Alessandro was an amazing driver. He was timely and attentive during the entire tour. The Mercedes van was newer and super clean. Montepulciano is a beautiful town to walk through. Alessandro set up the winery tour and tasting/lunch which turned out to be a private tour with our lovely host, Marta. It was a highlight of our vacation! The wine was superb. We went on to Pienza which is breathtaking then back to Florence at our doorstep.
Response from the operator: Dear Laura, Thank you very very much for your kind support! It's our goal to offer our guests only the best quality services. We are delighted to know that you enjoyed your day tour and that you had great time with your Professional Driver Alessandro! We look forward to showing you the rest of Italy in the future and to having you on board with us once again. Saluti from Rome, Best Rome Driver Team
via Viator
Tuscany transfer
Alex and Steffano were great drivers for our group. They were very timely and communcated well. Alex gave us good information along the route. They arranged a nice winery and lunch and adaptes well as we adjusted the schedule.
Response from the operator: Buongiorno! We truly thank you for your precious review and your support. It's always a pleasure to read that our guests are satisfied with the services we have provided them with! We look forward to showing you the rest of Italy in the future and to having you on board with us once again. Best Rome Driver Team
via Tripadvisor
Private Driver - Salvatore
We had Salvatore as our private driver for 1 week. He was amazing. The best driver we could ever have asked for. Kind, friendly, knowledgeable & an expert in the Italian regions we visited. He truly made our trip one to remember.
Response from the operator: Hello! We are so thrilled to receive such a wonderful and detailed review! We thank you very much for your feedback! We look forward to showing you the rest of Italy in the future and to have you on board with us once again. Saluti from Rome, Best Rome Driver Team
via Tripadvisor
Driver in Rome
I used Best Rone Driver while In Europe. Alex Paolino was my driver and he was excellent. He was on time and very knowledgeable of the surrounding areas. I highly recommend him!
Response from the operator: Hi Tommy! Thank you for your review! We are really pleased to hear that you had a great Rome experience with us and your trip went smoothly. We look forward to helping you plan more adventures in the future! Saluti from Rome, Best Rome Driver Team
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
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 4
- Verdict
- Worth a Look
Why this scores 56
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Montepulciano & Pienza Day Trip from Florence: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does Private Montepulciano & Pienza Day Trip from Florence cost?
+
Prices start at $763 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 Montepulciano & Pienza Day Trip from Florence take?
+
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 Private Montepulciano & Pienza Day Trip from Florence worth it?
+
It holds an Outty Ranking of 56 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 10 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 Montepulciano & Pienza Day Trip from Florence?
+
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 Montepulciano & Pienza Day Trip from Florence suitable for kids and families?
+
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 Private Montepulciano & Pienza Day Trip from Florence?
+
Around 4 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?
+
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 Private Montepulciano & Pienza Day Trip from Florence 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 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?
+
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?
+
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?
+
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.
Ready to lock in your spot?
Pick a date, choose your group, and see the exact price for Private Montepulciano & Pienza Day Trip from Florence.
Pick your date
